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Journal articles on the topic 'Organohalides'

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Author: Grafiati

Published: 7 July 2024

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1

Maucourt, Bruno, Stéphane Vuilleumier, and Françoise Bringel. "Transcriptional regulation of organohalide pollutant utilisation in bacteria." FEMS Microbiology Reviews 44, no. 2 (February 3, 2020): 189–207. http://dx.doi.org/10.1093/femsre/fuaa002.

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ABSTRACT Organohalides are organic molecules formed biotically and abiotically, both naturally and through industrial production. They are usually toxic and represent a health risk for living organisms, including humans. Bacteria capable of degrading organohalides for growth express dehalogenase genes encoding enzymes that cleave carbon-halogen bonds. Such bacteria are of potential high interest for bioremediation of contaminated sites. Dehalogenase genes are often part of gene clusters that may include regulators, accessory genes and genes for transporters and other enzymes of organohalide degradation pathways. Organohalides and their degradation products affect the activity of regulatory factors, and extensive genome-wide modulation of gene expression helps dehalogenating bacteria to cope with stresses associated with dehalogenation, such as intracellular increase of halides, dehalogenase-dependent acid production, organohalide toxicity and misrouting and bottlenecks in metabolic fluxes. This review focuses on transcriptional regulation of gene clusters for dehalogenation in bacteria, as studied in laboratory experiments and in situ. The diversity in gene content, organization and regulation of such gene clusters is highlighted for representative organohalide-degrading bacteria. Selected examples illustrate a key, overlooked role of regulatory processes, often strain-specific, for efficient dehalogenation and productive growth in presence of organohalides.

2

Lee, Matthew, Chris Marquis, Bat-Erdene Judger, and Mike Manefield. "Anaerobic microorganisms and bioremediation of organohalide pollution." Microbiology Australia 36, no. 3 (2015): 125. http://dx.doi.org/10.1071/ma15044.

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Organohalide pollution of subsurface environments is ubiquitous across all industrialised countries. Fortunately, strictly anaerobic microorganisms exist that have evolved using naturally occurring organohalides as their terminal electron acceptor. These unusual organisms are now being utilised to clean anthropogenic organohalide pollution.

3

Bolandi, Ali, Setare Tahmasebi Nick, and Sherine O. Obare. "Nanoscale materials for organohalide degradation via reduction pathways." Nanotechnology Reviews 1, no. 2 (March 1, 2012): 147–71. http://dx.doi.org/10.1515/ntrev-2012-0003.

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AbstractThe unique chemical and physical properties of nanoscale materials have led to important roles in several scientific and technological fields. Environmental chemistry processes have benefited from the enhanced reactivity of nanoscale particles relative to their bulk counterparts with contaminants. Here, we describe recent advances in the synthesis and characterization of metallic and bimetallic nanoparticles that have been effective toward degrading toxic organohalide contaminants. We then review the degradation mechanisms involved in the reactions of nanoscale particles with organohalides via reduction pathways. We also discuss an emerging area – the degradation of organohalides via multi-electron transfer pathways.

4

Bertolini, Martina, Sarah Zecchin, Giovanni Pietro Beretta, Patrizia De Nisi, Laura Ferrari, and Lucia Cavalca. "Effectiveness of Permeable Reactive Bio-Barriers for Bioremediation of an Organohalide-Polluted Aquifer by Natural-Occurring Microbial Community." Water 13, no. 17 (September 5, 2021): 2442. http://dx.doi.org/10.3390/w13172442.

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In this study, a bioremediation approach was evaluated for the decontamination of an aquifer affected by the release of organohalides by an industrial landfill. After preliminary physicochemical and microbiological characterization of the landfill groundwater, the stimulation of natural organohalide respiration by the addition of a reducing substrate (i.e., molasse) was tested both at microcosm and at field scales, by the placement of an anaerobic permeable reactive bio-barrier. Illumina sequencing of cDNA 16S rRNA gene revealed that organohalide-respiring bacteria of genera Geobacter, Sulfurospirillum, Dehalococcoides, Clostridium and Shewanella were present within the aquifer microbial community, along with fermentative Firmicutes and Parvarchaeota. Microcosm experiments confirmed the presence of an active natural attenuation, which was boosted by the addition of the reducing substrate. Field tests showed that the bio-barrier decreased the concentration of chloroethenes at a rate of 23.74 kg d−1. Monitoring of organohalide respiration biomarkers by qPCR and Illumina sequencing revealed that native microbial populations were involved in the dechlorination process, although their specific role still needs to be clarified. The accumulation of lower-chloroethenes suggested the need of future improvement of the present approach by supporting bacterial vinyl-chloride oxidation, to achieve a complete degradation of chloroethenes.

5

Futagami, Taiki, Yuki Morono, Takeshi Terada, Anna H. Kaksonen, and Fumio Inagaki. "Distribution of dehalogenation activity in subseafloor sediments of the Nankai Trough subduction zone." Philosophical Transactions of the Royal Society B: Biological Sciences 368, no. 1616 (April 19, 2013): 20120249. http://dx.doi.org/10.1098/rstb.2012.0249.

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Halogenated organic matter buried in marine subsurface sediment may serve as a source of electron acceptors for anaerobic respiration of subseafloor microbes. Detection of a diverse array of reductive dehalogenase-homologous ( rdhA ) genes suggests that subseafloor organohalide-respiring microbial communities may play significant ecological roles in the biogeochemical carbon and halogen cycle in the subseafloor biosphere. We report here the spatial distribution of dehalogenation activity in the Nankai Trough plate-subduction zone of the northwest Pacific off the Kii Peninsula of Japan. Incubation experiments with slurries of sediment collected at various depths and locations showed that degradation of several organohalides tested only occurred in the shallow sedimentary basin, down to 4.7 metres below the seafloor, despite detection of rdhA in the deeper sediments. We studied the phylogenetic diversity of the metabolically active microbes in positive enrichment cultures by extracting RNA, and found that Desulfuromonadales bacteria predominate. In addition, for the isolation of genes involved in the dehalogenation reaction, we performed a substrate-induced gene expression screening on DNA extracted from the enrichment cultures. Diverse DNA fragments were obtained and some of them showed best BLAST hit to known organohalide respirers such as Dehalococcoides , whereas no functionally known dehalogenation-related genes such as rdhA were found, indicating the need to improve the molecular approach to assess functional genes for organohalide respiration.

6

Ito, Hajime, Eiji Yamamoto, Satoshi Maeda, and Tetsuya Taketsugu. "Transition-Metal-Free Boryl Substitution Using Silylboranes and Alkoxy Bases." Synlett 28, no. 11 (April 26, 2017): 1258–67. http://dx.doi.org/10.1055/s-0036-1588772.

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Silylboranes are used as borylation reagents for organohalides in the presence of alkoxy bases without transition-metal catalysts. PhMe2Si–B(pin) reacts with a variety of aryl, alkenyl, and alkyl halides, including sterically hindered examples, to provide the corresponding organoboronates in good yields with high borylation/silylation ratios, showing good functional group compatibility. Halogenophilic attack of a silyl nucleophile on organohalides, and subsequent nucleophilic attack on the boron electrophile are identified to be crucial, based on the results of extensive theoretical and experimental studies. This borylation reaction is further applied to the first direct dimesitylboryl (BMes2) substitution of aryl halides using Ph2MeSi–BMes2 and Na(O-t-Bu), affording aryldimesitylboranes, which are regarded as an important class of compounds for organic materials.1 Introduction2 Boryl Substitution of Organohalides with PhMe2Si–B(pin)/Alkoxy Bases3 Mechanistic Investigations4 DFT Mechanistic Studies Using an Artificial Force Induced Reaction (AFIR) Method5 Dimesitylboryl Substitution of Aryl Halides with Ph2MeSi–BMes2/Na(O-t-Bu)6 Conclusion

7

Spurling, TH, and DA Winkler. "CNDO/2 Calculations for Organohalides." Australian Journal of Chemistry 39, no. 2 (1986): 233. http://dx.doi.org/10.1071/ch9860233.

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A CNDO/2 parameterization for performing semiempirical molecular orbital calculations for organic molecules containing bromine and iodine is presented; the results are superior to those from other parameterizations, and generally agree with ab initio calculations and experiment.

8

Wigginton, Nicholas S. "How bacteria break down organohalides." Science 346, no. 6208 (October 23, 2014): 435.9–436. http://dx.doi.org/10.1126/science.346.6208.435-i.

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9

Rupakula, Aamani, Thomas Kruse, Sjef Boeren, Christof Holliger, Hauke Smidt, and Julien Maillard. "The restricted metabolism of the obligate organohalide respiring bacterium Dehalobacter restrictus: lessons from tiered functional genomics." Philosophical Transactions of the Royal Society B: Biological Sciences 368, no. 1616 (April 19, 2013): 20120325. http://dx.doi.org/10.1098/rstb.2012.0325.

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Dehalobacter restrictus strain PER-K23 is an obligate organohalide respiring bacterium, which displays extremely narrow metabolic capabilities. It grows only via coupling energy conservation to anaerobic respiration of tetra- and trichloroethene with hydrogen as sole electron donor. Dehalobacter restrictus represents the paradigmatic member of the genus Dehalobacter , which in recent years has turned out to be a major player in the bioremediation of an increasing number of organohalides, both in situ and in laboratory studies. The recent elucidation of the D. restrictus genome revealed a rather elaborate genome with predicted pathways that were not suspected from its restricted metabolism, such as a complete corrinoid biosynthetic pathway, the Wood–Ljungdahl (WL) pathway for CO 2 fixation, abundant transcriptional regulators and several types of hydrogenases. However, one important feature of the genome is the presence of 25 reductive dehalogenase genes, from which so far only one, pceA , has been characterized on genetic and biochemical levels. This study describes a multi-level functional genomics approach on D. restrictus across three different growth phases. A global proteomic analysis allowed consideration of general metabolic pathways relevant to organohalide respiration, whereas the dedicated genomic and transcriptomic analysis focused on the diversity, composition and expression of genes associated with reductive dehalogenases.

10

Li, Sheng-Jun, Lu Han, and Shi-Kai Tian. "1,2-Aminohalogenation of arynes with amines and organohalides." Chemical Communications 55, no. 75 (2019): 11255–58. http://dx.doi.org/10.1039/c9cc05505c.

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11

Denk, Michael K., Nicholas S. Milutinović, Katherine M. Marczenko, Natalie M. Sadowski, and Athanasios Paschos. "Nature's hydrides: rapid reduction of halocarbons by folate model compounds." Chemical Science 8, no. 3 (2017): 1883–87. http://dx.doi.org/10.1039/c6sc04314c.

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12

Ghasemi, Mehri, Miaoqiang Lyu, Md Roknuzzaman, Jung-Ho Yun, Mengmeng Hao, Dongxu He, Yang Bai, et al. "Phenethylammonium bismuth halides: from single crystals to bulky-organic cation promoted thin-film deposition for potential optoelectronic applications." Journal of Materials Chemistry A 7, no. 36 (2019): 20733–41. http://dx.doi.org/10.1039/c9ta07454f.

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13

Kim, Hyejin, and Chulbom Lee. "Nickel-Catalyzed Reductive Cyclization of Organohalides." Organic Letters 13, no. 8 (April 15, 2011): 2050–53. http://dx.doi.org/10.1021/ol200455n.

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14

Xiao, Shuhuan, Chen Liu, Bin Song, Liang Wang, Yan Qi, and Yongjun Liu. "Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI." Chemical Communications 57, no. 50 (2021): 6169–72. http://dx.doi.org/10.1039/d1cc00965f.

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15

Kareem, Rzgar Tawfeeq, Bayan Azizi, Manzarbanou Asnaashariisfahani, Abdolghaffar Ebadi, and Esmail Vessally. "Vicinal halo-trifluoromethylation of alkenes." RSC Advances 11, no. 25 (2021): 14941–55. http://dx.doi.org/10.1039/d0ra06872a.

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Both trifluoromethyl and halide groups are widely found in medicinally and pharmaceutically important compounds and, moreover, organohalides are commonly used as versatile intermediates in synthetic organic chemistry.

16

Sun, Baozhen, Shuang Liu, Mengru Zhang, Jinbo Zhao, and Qian Zhang. "Pd-Catalyzed carboannulation of γ,δ-alkenyl oximes: efficient access to 5-membered cyclic nitrones and dihydroazines." Organic Chemistry Frontiers 6, no. 3 (2019): 388–92. http://dx.doi.org/10.1039/c8qo01076e.

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17

Zhang, Haoxiang, Mengze Liang, Xiao Zhang, Meng-Ke He, Chao Yang, Lin Guo, and Wujiong Xia. "Electrochemical synthesis of functionalized gem-difluoroalkenes with diverse alkyl sources via a defluorinative alkylation process." Organic Chemistry Frontiers 9, no. 1 (2022): 95–101. http://dx.doi.org/10.1039/d1qo01460a.

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An electrochemical defluorinative alkylation of α-trifluoromethyl alkenes is described. This reaction enables the preparation of functionalized gem-difluoroalkenes with diverse alkyl sources including organohalides, NHP esters, and Katritzky salts.

18

Xu, Qing, Huamei Xie, Pingliang Chen, Lei Yu, Jianhui Chen, and Xingen Hu. "Organohalide-catalyzed dehydrative O-alkylation between alcohols: a facile etherification method for aliphatic ether synthesis." Green Chemistry 17, no. 5 (2015): 2774–79. http://dx.doi.org/10.1039/c5gc00284b.

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Organohalides effectively catalyzed dehydrative O-alkylation reactions between alcohols, providing selective, practical, green, and easily scalable homo- and cross-etherification methods for the preparation of useful symmetrical and unsymmetrical aliphatic ethers.

19

Fagin, Anatolii A., Tatyana V. Balashova, Dmitrii M. Kusyaev, Tatyana I. Kulikova, Tatyana A. Glukhova, Natalya P. Makarenko, Yurii A. Kurskii, William J. Evans, and Mikhail N. Bochkarev. "Reactions of neodymium(II) iodide with organohalides." Polyhedron 25, no. 5 (March 2006): 1105–10. http://dx.doi.org/10.1016/j.poly.2005.08.050.

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20

Chu, Xue-Qiang, Dan Liu, Zhen-Hua Xing, Xiao-Ping Xu, and Shun-Jun Ji. "Palladium-Catalyzed Cyclization of Alkenes with Organohalides." Organic Letters 18, no. 4 (February 2, 2016): 776–79. http://dx.doi.org/10.1021/acs.orglett.6b00035.

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21

Root, Douglas P., Gerald Pitz, and Namal Priyantha. "Electrocatalytic metalloporphyrin electrode for detection of organohalides." Electrochimica Acta 36, no. 5-6 (January 1991): 855–58. http://dx.doi.org/10.1016/0013-4686(91)85285-f.

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22

Pri-Bar, Ilan, and Ouri Buchman. "Homogeneous, palladium-catalyzed, selective hydrogenolysis of organohalides." Journal of Organic Chemistry 51, no. 5 (March 1986): 734–36. http://dx.doi.org/10.1021/jo00355a029.

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23

Boateng, Sakyiwaa. "Assessing conceptual difficulties experienced by pre-service chemistry teachers in organic chemistry." Eurasia Journal of Mathematics, Science and Technology Education 20, no. 2 (February 1, 2024): em2398. http://dx.doi.org/10.29333/ejmste/14156.

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Organic chemistry is a mandatory component of chemistry II and chemistry III within the curriculum for pre-service chemistry teachers (PSCTs) pursuing a degree in chemistry teaching. The organic chemistry course sequence is well recognized as challenging and unapproachable for students, despite its significant relevance and impact across several sectors. While efforts have been made to recognize and deal with challenges faced by students in the cognitive and psychomotor aspects, there has been less attention given to identifying PSCTs’ conceptual difficulties and misconceptions of organic chemistry. This includes the subsequent strategies to design instructions to enhance students’ learning experiences, which are crucial elements in addressing their achievements in organic chemistry. The study aimed to identify the conceptual difficulties and misconceptions encountered by PSCTs in organohalides and stereochemistry. Furthermore, the study aimed to suggest strategies to enhance PSCTs’ understanding of the course. The study was situated within the theoretical framework of constructivism and employed an interpretivist qualitative case study design. The population under study consisted of all individuals who were enrolled in the Bachelor of Education program within the faculty of educational sciences. A cohort of 33 whole-class PSCTs who had registered for the chemistry III course, where organohalides and stereochemistry were taught as units, were purposefully selected to participate in the study. The main instruments were document analysis, formal written tests, and interviews. Data were analyzed using thematic analysis. The study revealed that PSCTs encountered difficulties when attempting to solve problems related to organohalides and stereochemistry. In addition, PSCTs had misconceptions about these concepts. The study, therefore, recommends the implementation of suitable and appropriate instructional strategies to enhance PSCTs’ conceptual understanding and reduce misconceptions.

24

Bauman, Lew, and Michael K. Stenstrom. "Observations of the reaction between organohalides and sulfite." Environmental Science & Technology 23, no. 2 (February 1989): 232–36. http://dx.doi.org/10.1021/es00179a017.

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25

Kim, Hyejin, and Chulbom Lee. "Visible-Light-Induced Photocatalytic Reductive Transformations of Organohalides." Angewandte Chemie 124, no. 49 (November 4, 2012): 12469–72. http://dx.doi.org/10.1002/ange.201203599.

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26

Lekkala, Ravindar, Revathi Lekkala, Balakrishna Moku, K. P. Rakesh, and Hua-Li Qin. "Recent Developments in Radical-Mediated Transformations of Organohalides." European Journal of Organic Chemistry 2019, no. 17 (April 12, 2019): 2769–806. http://dx.doi.org/10.1002/ejoc.201900098.

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27

Kim, Hyejin, and Chulbom Lee. "Visible-Light-Induced Photocatalytic Reductive Transformations of Organohalides." Angewandte Chemie International Edition 51, no. 49 (November 4, 2012): 12303–6. http://dx.doi.org/10.1002/anie.201203599.

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28

Kim, Hyejin, and Chulbom Lee. "ChemInform Abstract: Nickel-Catalyzed Reductive Cyclizaton of Organohalides." ChemInform 42, no. 30 (June 30, 2011): no. http://dx.doi.org/10.1002/chin.201130030.

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29

Abbaspourtamijani, Ali, Nicholas Vitti, Henry White, and Yue Qi. "Electrochemical Reduction of Organohalides: Insights from First Principles Calculations." ECS Meeting Abstracts MA2021-02, no. 48 (October 19, 2021): 1940. http://dx.doi.org/10.1149/ma2021-02481940mtgabs.

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30

He, Haozheng, Yiyang Li, Rui Shen, Hojae Shim, Yanhong Zeng, Siyan Zhao, Qihong Lu, Bixian Mai, and Shanquan Wang. "Environmental occurrence and remediation of emerging organohalides: A review." Environmental Pollution 290 (December 2021): 118060. http://dx.doi.org/10.1016/j.envpol.2021.118060.

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31

Lu, Qihong, Lan Qiu, Ling Yu, Shangwei Zhang, Renata Alves de Toledo, Hojae Shim, and Shanquan Wang. "Microbial transformation of chiral organohalides: Distribution, microorganisms and mechanisms." Journal of Hazardous Materials 368 (April 2019): 849–61. http://dx.doi.org/10.1016/j.jhazmat.2019.01.103.

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32

Wallner, Olov A., and Kálmán J. Szabó. "Employment of Palladium Pincer-Complexes in Phenylselenylation of Organohalides." Journal of Organic Chemistry 70, no. 23 (November 2005): 9215–21. http://dx.doi.org/10.1021/jo051266x.

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33

Cheung, Man Sing, Todd B. Marder, and Zhenyang Lin. "Mechanisms of Reactions of a Lithium Boryl with Organohalides." Organometallics 30, no. 11 (June 13, 2011): 3018–28. http://dx.doi.org/10.1021/om200115y.

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34

Zanaroli, Giulio, Andrea Negroni, Max M. Häggblom, and Fabio Fava. "Microbial dehalogenation of organohalides in marine and estuarine environments." Current Opinion in Biotechnology 33 (June 2015): 287–95. http://dx.doi.org/10.1016/j.copbio.2015.03.013.

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35

Nijenhuis, Ivonne, and Hans H. Richnow. "Stable isotope fractionation concepts for characterizing biotransformation of organohalides." Current Opinion in Biotechnology 41 (October 2016): 108–13. http://dx.doi.org/10.1016/j.copbio.2016.06.002.

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36

Li, Yuqiang, and Guoyin Yin. "Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Coupling of Two sp2-Hybridized Organohalides." Synlett 32, no. 16 (August 24, 2021): 1657–61. http://dx.doi.org/10.1055/a-1608-5693.

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AbstractCross-coupling reactions are essential for the synthesis of complex organic molecules. Here, we report a nickel-catalyzed Ullmann cross-coupling of two sp2-hybridized organohalides, featuring high cross-selectivity when the two coupling partners are used in a 1:1 ratio. The high chemoselectivity is governed by the bathocuproine ligand. Moreover, the mild reductive reaction conditions allow that a wide range of functional groups are compatible in this Ullmann cross-coupling.

37

Wackett, Lawrence P. "Recruitment of Co-Metabolic Enzymes for Environmental Detoxification of Organohalides." Environmental Health Perspectives 103 (June 1995): 45. http://dx.doi.org/10.2307/3432478.

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38

Wackett, L. P. "Recruitment of co-metabolic enzymes for environmental detoxification of organohalides." Environmental Health Perspectives 103, suppl 5 (June 1995): 45–48. http://dx.doi.org/10.1289/ehp.95103s445.

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39

Cristofoli, Walter A., and Brian A. Keay. "A palladium catalyzed cross-coupling between furylborates (generated ) and organohalides." Tetrahedron Letters 32, no. 42 (October 1991): 5881–84. http://dx.doi.org/10.1016/s0040-4039(00)79416-0.

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40

Zheng, Kewang, Guanlin Xiao, Tao Guo, Yalan Ding, Chengdong Wang, Teck-Peng Loh, and Xiaojin Wu. "Intermolecular Reductive Heck Reaction of Unactivated Aliphatic Alkenes with Organohalides." Organic Letters 22, no. 2 (January 8, 2020): 694–99. http://dx.doi.org/10.1021/acs.orglett.9b04474.

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41

Jugder, Bat-Erdene, Haluk Ertan, Matthew Lee, Michael Manefield, and Christopher P. Marquis. "Reductive Dehalogenases Come of Age in Biological Destruction of Organohalides." Trends in Biotechnology 33, no. 10 (October 2015): 595–610. http://dx.doi.org/10.1016/j.tibtech.2015.07.004.

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42

Kim, Hyejin, and Chulbom Lee. "ChemInform Abstract: Visible Light Induced Photocatalytic Reductive Transformations of Organohalides." ChemInform 44, no. 22 (May 13, 2013): no. http://dx.doi.org/10.1002/chin.201322033.

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43

Huang, Yu, Ruizhi Yang, and Wenbo H. Liu. "Recent advances of the Grignard-type reactions without involving organohalides." Tetrahedron Chem 9 (March 2024): 100069. http://dx.doi.org/10.1016/j.tchem.2024.100069.

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44

Tang, Shuang-Qi, Martine Schmitt, and Frédéric Bihel. "POxAP Precatalysts and the Negishi Cross-Coupling Reaction." Synthesis 52, no. 01 (October 28, 2019): 51–59. http://dx.doi.org/10.1055/s-0039-1690728.

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Recently developed for the Fukuyama reaction, post-oxidative addition precatalysts (POxAPs) are also very efficient in catalyzing Negishi cross-coupling reactions between organohalides and organozinc reagents. Using very low catalyst loadings, POxAPs show similar catalytic activities to those of classical precatalysts such as XPhos Pd G4 or PEPPSI-IPr, with turnover numbers of up to 93,000. POxAPs are easily prepared, are stable to air and moisture, tolerate a wide range of functional groups in the Negishi cross-coupling reaction and contribute advantageously to the arsenal of organic chemists in terms of Pd precatalysts.

45

Kohn, Tamar, and A. Lynn Roberts. "Interspecies Competitive Effects in Reduction of Organohalides in Connelly Iron Columns." Environmental Engineering Science 23, no. 5 (September 2006): 874–85. http://dx.doi.org/10.1089/ees.2006.23.874.

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46

Liu, Yongjun, Shuhuan Xiao, Yan Qi, and Feng Du. "Reductive Homocoupling of Organohalides Using Nickel(II) Chloride and Samarium Metal." Chemistry - An Asian Journal 12, no. 6 (February 21, 2017): 673–78. http://dx.doi.org/10.1002/asia.201601712.

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47

Gilbert, Bruce C., Richard J. Harrison, Chris I. Lindsay, P. Terry McGrail, Andrew F. Parsons, Richard Southward, and Derek J. Irvine. "Polymerization of Methyl Methacrylate Using Dimanganese Decacarbonyl in the Presence of Organohalides." Macromolecules 36, no. 24 (December 2003): 9020–23. http://dx.doi.org/10.1021/ma034712w.

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48

Falck, J. R., Rama K. Bhatt, and Jianhua Ye. "Tin-Copper Transmetalation: Cross-Coupling of .alpha.-Heteroatom-Substituted Alkyltributylstannanes with Organohalides." Journal of the American Chemical Society 117, no. 22 (June 1995): 5973–82. http://dx.doi.org/10.1021/ja00127a010.

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49

Shrestha, Bijay, Surendra Thapa, Santosh K. Gurung, Ryan A. S. Pike, and Ramesh Giri. "General Copper-Catalyzed Coupling of Alkyl-, Aryl-, and Alkynylaluminum Reagents with Organohalides." Journal of Organic Chemistry 81, no. 3 (January 20, 2016): 787–802. http://dx.doi.org/10.1021/acs.joc.5b02077.

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Zhang, Ting-Ting, Mu-Jia Luo, Yang Li, Ren-Jie Song, and Jin-Heng Li. "Electrochemical Alkoxyhalogenation of Alkenes with Organohalides as the Halide Sources via Dehalogenation." Organic Letters 22, no. 18 (August 27, 2020): 7250–54. http://dx.doi.org/10.1021/acs.orglett.0c02582.

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