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Journal articles on the topic 'Alkynoate'

Author: Grafiati
Published: 6 September 2023

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1

Zeng, Yao-Fu, Dong-Hang Tan, Yunyun Chen, Wen-Xin Lv, Xu-Ge Liu, Qingjiang Li, and Honggen Wang. "Direct radical trifluoromethylthiolation and thiocyanation of aryl alkynoate esters: mild and facile synthesis of 3-trifluoromethylthiolated and 3-thiocyanated coumarins." Organic Chemistry Frontiers 2, no. 11 (2015): 1511–15. http://dx.doi.org/10.1039/c5qo00271k.

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2

Aparece, Mark D., and Paul A. Vadola. "Gold-Catalyzed Dearomative Spirocyclization of Aryl Alkynoate Esters." Organic Letters 16, no. 22 (November 3, 2014): 6008–11. http://dx.doi.org/10.1021/ol503022h.

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3

Song, Zefeng, Weijia Wang, Zhixin Liu, Yue Lu, and De Wang. "Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with para-Quinone Methides." Journal of Organic Chemistry 86, no. 13 (June 24, 2021): 8590–99. http://dx.doi.org/10.1021/acs.joc.1c00226.

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4

Valette, Damien, Yajing Lian, John P. Haydek, Kenneth I. Hardcastle, and Huw M. L. Davies. "Alkynoate Synthesis through the Vinylogous Reactivity of Rhodium(II) Carbenoids." Angewandte Chemie 124, no. 34 (July 16, 2012): 8764–67. http://dx.doi.org/10.1002/ange.201204047.

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5

Aparece, Mark D., and Paul A. Vadola. "ChemInform Abstract: Gold-Catalyzed Dearomative Spirocyclization of Aryl Alkynoate Esters." ChemInform 46, no. 18 (April 16, 2015): no. http://dx.doi.org/10.1002/chin.201518113.

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6

Valette, Damien, Yajing Lian, John P. Haydek, Kenneth I. Hardcastle, and Huw M. L. Davies. "Alkynoate Synthesis through the Vinylogous Reactivity of Rhodium(II) Carbenoids." Angewandte Chemie International Edition 51, no. 34 (July 16, 2012): 8636–39. http://dx.doi.org/10.1002/anie.201204047.

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7

Imagawa, Hiroshi, Atsushi Kinoshita, Takashi Fukuyama, Hirofumi Yamamoto, and Mugio Nishizawa. "Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group." Tetrahedron Letters 47, no. 27 (July 2006): 4729–31. http://dx.doi.org/10.1016/j.tetlet.2006.04.114.

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8

Schäfer, Christian, Michel Miesch, and Laurence Miesch. "Intramolecular reductive ketone–alkynoate coupling reaction promoted by (η2-propene)titanium." Organic & Biomolecular Chemistry 10, no. 16 (2012): 3253. http://dx.doi.org/10.1039/c2ob07049a.

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9

Valette, Damien, Yajing Lian, John P. Haydek, Kenneth I. Hardcastle, and Huw M. L. Davies. "ChemInform Abstract: Alkynoate Synthesis Through the Vinylogous Reactivity of Rhodium(II) Carbenoids." ChemInform 44, no. 3 (January 15, 2013): no. http://dx.doi.org/10.1002/chin.201303045.

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10

Schaefer, Christian, Michel Miesch, and Laurence Miesch. "ChemInform Abstract: Intramolecular Reductive Ketone-Alkynoate Coupling Reaction Promoted by (η2-Propene)titanium." ChemInform 43, no. 38 (August 23, 2012): no. http://dx.doi.org/10.1002/chin.201238029.

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11

Brecker, Lothar, Julia Petschnigg, Nicole Depine, Hansjorg Weber, and Douglas W. Ribbons. "In situ proton NMR analysis of alpha-alkynoate biotransformations. From 'invisible' substrates to detectable metabolites." European Journal of Biochemistry 270, no. 7 (April 2003): 1393–98. http://dx.doi.org/10.1046/j.1432-1033.2003.03460.x.

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12

Song, Bo, Rongyuan Zhang, Rong Hu, Xu Chen, Dongming Liu, Jiali Guo, Xiaotian Xu, Anjun Qin, and Ben Zhong Tang. "Site‐Selective, Multistep Functionalizations of CO 2 ‐Based Hyperbranched Poly(alkynoate)s toward Functional Polymetric Materials." Advanced Science 7, no. 17 (July 8, 2020): 2000465. http://dx.doi.org/10.1002/advs.202000465.

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13

Zhang, Jiayong, Cheng Cheng, Dian Wang, and Zhiwei Miao. "Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3 + 2] Annulation of Methyleneindolinone with Alkynoate Derivatives." Journal of Organic Chemistry 82, no. 19 (September 21, 2017): 10121–28. http://dx.doi.org/10.1021/acs.joc.7b01582.

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14

Luo, Zaigang, Yuyu Fang, Yu Zhao, Peng Liu, Xuemei Xu, Chengtao Feng, Zhong Li, and Jie He. "Synthesis of multisubstituted furans via Cu(i)-catalyzed annulation of ketones with alkynoate under ligand- and additive-free conditions." RSC Advances 6, no. 7 (2016): 5436–41. http://dx.doi.org/10.1039/c5ra23058f.

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A simple and efficient Cu(i)-catalyzed strategy for synthesis of mutisubstituted furans has been developed and this ligand- and additive-free annulation method is well suitable for both nonactivated arylmethyl ketones 1,3-dicarbonyl compounds.
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15

Kamijo, Shin, Kaori Kamijo, Daiki Magarifuchi, Ryota Ozawa, Keisuke Tao, and Toshihiro Murafuji. "Two-directional carbon chain elongation via the consecutive 1,4-addition of allyl malononitrile and the Cope rearrangement on an alkynoate platform." Tetrahedron Letters 57, no. 1 (January 2016): 137–40. http://dx.doi.org/10.1016/j.tetlet.2015.11.081.

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16

Zeng, Yao-Fu, Dong-Hang Tan, Yunyun Chen, Wen-Xin Lv, Xu-Ge Liu, Qingjiang Li, and Honggen Wang. "ChemInform Abstract: Direct Radical Trifluoromethylthiolation and Thiocyanation of Aryl Alkynoate Esters: Mild and Facile Synthesis of 3-Trifluoromethylthiolated and 3-Thiocyanated Coumarins." ChemInform 47, no. 13 (March 2016): no. http://dx.doi.org/10.1002/chin.201613151.

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17

Che, Jiuwei, Alavala Gopi Krishna Reddy, Li Niu, Dong Xing, and Wenhao Hu. "Cu(I)-Catalyzed Three-Component Reaction of α-Diazo Amide with Terminal Alkyne and Isatin Ketimine via Electrophilic Trapping of Active Alkynoate-Copper Intermediate." Organic Letters 21, no. 12 (June 3, 2019): 4571–74. http://dx.doi.org/10.1021/acs.orglett.9b01470.

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18

Zhu, Mei, Weijun Fu, Zhiqiang Wang, Chen Xu, and Baoming Ji. "Visible-light-mediated direct difluoromethylation of alkynoates: synthesis of 3-difluoromethylated coumarins." Organic & Biomolecular Chemistry 15, no. 43 (2017): 9057–60. http://dx.doi.org/10.1039/c7ob02366a.

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19

Zhang, Wei, Chen Yang, Yu-Liang Pan, Xin Li, and Jin-Pei Cheng. "Synthesis of 3-cyanomethylated coumarins by a visible-light-mediated direct cyanomethylation of aryl alkynoates." Organic & Biomolecular Chemistry 16, no. 32 (2018): 5788–92. http://dx.doi.org/10.1039/c8ob01513a.

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20

Kong, Hongjun, Qingrui Li, Yunnian Yin, Mengmeng Huang, Jung Keun Kim, Yu Zhu, Yabo Li, and Yangjie Wu. "An efficient light on–off one-pot method for the synthesis of 3-styryl coumarins from aryl alkynoates." Organic & Biomolecular Chemistry 17, no. 18 (2019): 4621–28. http://dx.doi.org/10.1039/c9ob00421a.

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21

Li, Huan, Shuai Liu, Yangen Huang, Xiu-Hua Xu, and Feng-Ling Qing. "Tandem trifluoromethylthiolation/aryl migration of aryl alkynoates to trifluoromethylthiolated alkenes." Chemical Communications 53, no. 73 (2017): 10136–39. http://dx.doi.org/10.1039/c7cc06232j.

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22

Davey, Stephen. "Addition to alkynoates." Nature Chemistry 6, no. 9 (August 21, 2014): 754. http://dx.doi.org/10.1038/nchem.2051.

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23

Li, Qingrui, Yunnian Yin, Yabo Li, Jianye Zhang, Mengmeng Huang, Jung Keun Kim, and Yangjie Wu. "A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate." Organic Chemistry Frontiers 6, no. 18 (2019): 3238–43. http://dx.doi.org/10.1039/c9qo00795d.

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24

Khan, Imtiaz, Sumera Zaib, and Aliya Ibrar. "New frontiers in the transition-metal-free synthesis of heterocycles from alkynoates: an overview and current status." Organic Chemistry Frontiers 7, no. 22 (2020): 3734–91. http://dx.doi.org/10.1039/d0qo00698j.

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25

Kong, De-Long, Liang Cheng, Hong-Ru Wu, Yang-Xiong Li, Dong Wang, and Li Liu. "A metal-free yne-addition/1,4-aryl migration/decarboxylation cascade reaction of alkynoates with Csp3–H centers." Organic & Biomolecular Chemistry 14, no. 7 (2016): 2210–17. http://dx.doi.org/10.1039/c5ob02478a.

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26

Feng, Shangbiao, Jinlai Li, Zaimin Liu, Haiyu Sun, Hongliang Shi, Xiaolei Wang, Xingang Xie, and Xuegong She. "Visible-light-mediated radical cascade reaction: synthesis of 3-bromocoumarins from alkynoates." Org. Biomol. Chem. 15, no. 41 (2017): 8820–26. http://dx.doi.org/10.1039/c7ob02199b.

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27

Li, Zun, Jia Zheng, Weigao Hu, Jianxiao Li, Wanqing Wu, and Huanfeng Jiang. "Synthesis of 1,4-enyne-3-ones via palladium-catalyzed sequential decarboxylation and carbonylation of allyl alkynoates." Organic Chemistry Frontiers 4, no. 7 (2017): 1363–66. http://dx.doi.org/10.1039/c7qo00082k.

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28

Wang, Qiumei, Chao Yang, and Chao Jiang. "Visible-light-promoted radical acylation/cyclization of alkynoates with aldehydes for the synthesis of 3-acylcoumarins." Organic & Biomolecular Chemistry 16, no. 43 (2018): 8196–204. http://dx.doi.org/10.1039/c8ob02232a.

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29

Pan, Changduo, Rongzhen Chen, Weile Shao, and Jin-Tao Yu. "Metal-free radical addition/cyclization of alkynoates with xanthates towards 3-(β-carbonyl)coumarins." Organic & Biomolecular Chemistry 14, no. 38 (2016): 9033–39. http://dx.doi.org/10.1039/c6ob01732k.

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30

Chen, Pu, Zan Chen, Bi-Quan Xiong, Yun Liang, Ke-Wen Tang, Jun Xie, and Yu Liu. "Visible-light-mediated cascade cyanoalkylsulfonylation/cyclization of alkynoates leading to coumarins via SO2 insertion." Organic & Biomolecular Chemistry 19, no. 14 (2021): 3181–90. http://dx.doi.org/10.1039/d1ob00142f.

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A visible-light-mediated cascade cyanoalkylsulfonylation/cyclization of alkynoates with cycloketone oxime compounds for the preparation of 3-cyanoalkylsulfonylcoumarins via SO2 insertion is reported.
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31

Chen, Yan-Shan, Yu Zheng, Zhi-Jun Chen, Zhen-Zhen Xie, Xian-Chen He, Jun-An Xiao, Kai Chen, Hao-Yue Xiang, and Hua Yang. "A phosphine-catalysed one-pot domino sequence to access cyclopentene-fused coumarins." Organic & Biomolecular Chemistry 19, no. 32 (2021): 7074–80. http://dx.doi.org/10.1039/d1ob01143j.

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A novel phosphine-catalysed, one-pot domino approach for the annulation of 2-formylphenyl alkynoates with activated methylene compounds to construct various cyclopentene-fused dihydrocoumarins has been developed.
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32

Wei, Wei, Leilei Wang, Huilan Yue, Yuan-Ye Jiang, and Daoshan Yang. "Catalyst-free synthesis of α-thioacrylic acids via cascade thiolation and 1,4-aryl migration of aryl alkynoates at room temperature." Organic & Biomolecular Chemistry 16, no. 37 (2018): 8379–83. http://dx.doi.org/10.1039/c8ob01349g.

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33

Heinrich, Clément F., Michel Miesch, and Laurence Miesch. "In situ intramolecular catalytic 1,2-addition of allenoates to cyclic ketones towards polycyclic allenoates." Organic & Biomolecular Chemistry 13, no. 7 (2015): 2153–56. http://dx.doi.org/10.1039/c4ob02451f.

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34

Eşsiz, Selçuk. "A computational study for the reaction mechanism of metal-free cyanomethylation of aryl alkynoates with acetonitrile." RSC Advances 11, no. 30 (2021): 18246–51. http://dx.doi.org/10.1039/d1ra01649k.

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A computational study of metal-free cyanomethylation and cyclization of aryl alkynoates with acetonitrile is carried out employing density functional theory and high-level coupled-cluster methods, such as [CCSD(T)].
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35

Sau, Sudip, and Prasenjit Mal. "3-Nitro-coumarin synthesis via nitrative cyclization of aryl alkynoates using tert-butyl nitrite." Chemical Communications 57, no. 73 (2021): 9228–31. http://dx.doi.org/10.1039/d1cc03415d.

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36

Jennings, M., and A. Hendrix. "Catalytic Carbocupration of Alkynoates." Synfacts 2010, no. 09 (August 23, 2010): 1032. http://dx.doi.org/10.1055/s-0030-1257956.

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37

Liu, Tong, Qiuping Ding, Qianshou Zong, and Guanyinsheng Qiu. "Radical 5-exo cyclization of alkynoates with 2-oxoacetic acids for synthesis of 3-acylcoumarins." Organic Chemistry Frontiers 2, no. 6 (2015): 670–73. http://dx.doi.org/10.1039/c5qo00029g.

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A silver-promoted decarboxylative annulation of alkynoates with 2-oxoacetic acids leading to the formation of 3-acyl-4-arylcoumarins is reported. The process involves radical decarboxylative acylation, 5-exo cyclization, and ester migration.
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38

Piers, Edward, Timothy Wong, Philip D. Coish, and Christine Rogers. "A convenient procedure for the efficient preparation of alkyl (Z)-3-iodo-2-alkenoates." Canadian Journal of Chemistry 72, no. 8 (August 1, 1994): 1816–19. http://dx.doi.org/10.1139/v94-230.

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39

Zeng, Piaopiao, Xiaoxiao Huang, Wei Tang, and Zhiwei Chen. "Copper-catalyzed cascade radical cyclization of alkynoates: construction of aryldifluoromethylated coumarins." Organic & Biomolecular Chemistry 19, no. 46 (2021): 10223–27. http://dx.doi.org/10.1039/d1ob01754c.

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Synthesis of a variety of aryldifluoromethylated coumarins by cascade radical cyclization reactions in systems where alkynoates and α,α-difluoroarylacetic acids coexist, using (NH4)2S2O8 as oxidant and CuI as catalyst. The transformation was accomplished under mild conditions.
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40

Qiu, Guanyinsheng, Tong Liu, and Qiuping Ding. "Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone." Organic Chemistry Frontiers 3, no. 4 (2016): 510–15. http://dx.doi.org/10.1039/c6qo00041j.

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A K2S2O8-mediated tandem radical brominative addition of alkynoates, oxidative spiro-cyclization, and 1,2-migration of esters is reported for the synthesis of 3-bromocoumarins with high efficiency.
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41

Ni, Shengyang, Jia Cao, Haibo Mei, Jianlin Han, Shuhua Li, and Yi Pan. "Sunlight-promoted cyclization versus decarboxylation in the reaction of alkynoates with N-iodosuccinimide: easy access to 3-iodocoumarins." Green Chemistry 18, no. 14 (2016): 3935–39. http://dx.doi.org/10.1039/c6gc01027j.

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We report the green, sunlight-initiated radical conversion of aryl alkynoates to 3-iodocoumarins using NIS without the use of a catalyst or additive. Mechanistic studies indicate that the reaction proceeds through iodination, spirocyclization and ring expansion to form the kinetic product.
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42

Piers, Edward, Timothy Wong, and Keith A. Ellis. "Use of lithium (trimethylstannyl)(cyano)cuprate for the conversion of alkyl 2-alkynoates into alkyl (Z)- and (E)-3-trimethylstannyl-2-alkenoates." Canadian Journal of Chemistry 70, no. 7 (July 1, 1992): 2058–64. http://dx.doi.org/10.1139/v92-260.

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Reaction of functionalized alkyl 2-alkynoates (e.g., 13–19) with lithium (trimethylstannyl)(cyano)cuprate (3) under two sets of carefully defined experimental conditions provides, efficiently and stereoselectively, either alkyl (Z)- or (E)-3-trimethylstannyl-2-alkenoates (e.g., 23, 26–31 and 24, 32–37, respectively).
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43

Luo, Zaigang, Xinxin Han, Chenfu Liu, Qiannan Liu, Rui Li, Peng Liu, and Xuemei Xu. "Catalyst-Free Synthesis of 1,4-Dihydroquinolines and Pyrrolo[1,2-a]quinolines via Intermolecular [4+2]/[3+2] Radical Cyclization of N-Methylanilines with Alkynoates." Synthesis 52, no. 07 (January 2, 2020): 1067–75. http://dx.doi.org/10.1055/s-0039-1691541.

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Intermolecular [4+2]/[3+2] radical annulation of N-methyl­anilines with alkynoates under metal- and photoredox-catalyst-free conditions provides a practical and efficient method to synthesize bioactive 1,4-dihydroquinolines and pyrrolo[1,2-a]quinolines in one pot in moderate to high overall yields.
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44

Kolesinska, Beata. "P-Acylphosphonium salts and their vinyloges — application in synthesis." Open Chemistry 8, no. 6 (December 1, 2010): 1147–71. http://dx.doi.org/10.2478/s11532-010-0114-z.

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AbstractReview with 101 refs. of progress in synthetic applications and properties of P-acylphosphonium salts including acylation via P-acylphosphonium salts, enantioselective acylation using chiral phosphine ligands, nucleophilic (β)-oniovinylation, and reaction involving vinyloges of P-acylphosphonium salts formed by treatment conjugated alkenoates or alkynoates with phosphines.
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45

Wakamatsu, Takamichi, Kazunori Nagao, Hirohisa Ohmiya, and Masaya Sawamura. "Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates." Beilstein Journal of Organic Chemistry 11 (December 4, 2015): 2444–50. http://dx.doi.org/10.3762/bjoc.11.265.

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A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form β-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless of the substrate structure. A variety of functional groups were compatible with the conjugate addition.
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46

Lu, Xiyan, Yishu Du, and Cheng Lu. "Synthetic methodology using tertiary phosphines as nucleophilic catalysts." Pure and Applied Chemistry 77, no. 12 (January 1, 2005): 1985–90. http://dx.doi.org/10.1351/pac200577121985.

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Allenoates or 2-alkynoates are known to react with tertiary phosphines to form the phosphine-substituted 1,3-dipoles, which can react with various substrates with the simultaneous elimination of the tertiary phosphine. The reaction is catalytic to the tertiary phosphine used. The investigation of the appropriate dipolarophiles and the further extension of this reaction are discussed.
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47

Murayama, Hiroaki, Kazunori Nagao, Hirohisa Ohmiya, and Masaya Sawamura. "Phosphine-Catalyzed Vicinal Acylcyanation of Alkynoates." Organic Letters 18, no. 7 (March 24, 2016): 1706–9. http://dx.doi.org/10.1021/acs.orglett.6b00677.

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48

Lu, Xiyan, and Qinghai Zhang. "Effect of ligands on the divalent palladium- catalyzed carbon-carbon coupling reactions. Highly enantioselective synthesis of optically active g-butyrolactones." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 247–50. http://dx.doi.org/10.1351/pac200173020247.

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In the palladium (II) -catalyzed enyne coupling reactions, the nitrogen-containing ligand plays the same role as the halide ion to inhibit the β-hydride elimination. Employing the pymox or bisoxazoline as ligands, the catalytic asymmetric cyclization of (Z) -4'-acetoxy-2'-butenyl 2-alkynoates initiated by acetoxypalladation was established with high efficiency (up to 92% ee) to afford the optically active γ-butyrolactones.
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49

Høyer, Thomas, Anders Kjær, and Jens Lykkesfeldt. "A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones." Collection of Czechoslovak Chemical Communications 56, no. 5 (1991): 1042–51. http://dx.doi.org/10.1135/cccc19911042.

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The tert-butyl propiolate ion serves as a convenient and efficient nucleophile in boron trifluoride-catalyzed openings of homochiral, mono-substituted epoxides. The resulting tert-butyl 5-hydroxy-2-alkynoates are converted into the title compounds upon semihydrogenation followed by acid hydrolysis. Specific examples include the synthesis of parasorbic acid and massoilactone, two naturally derived lactones of the present type. The scope of the synthetic protocol is discussed.
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50

Kim, Myung Hyun, Jaewon Choi, Kyoung Chul Ko, Kyoungil Cho, Ji Hoon Park, Sang Moon Lee, Hae Jin Kim, Yoon-Joo Ko, Jin Yong Lee, and Seung Uk Son. "Network-controlled unique reactivities of carbonyl groups in hollow and microporous organic polymer." Chemical Communications 54, no. 40 (2018): 5134–37. http://dx.doi.org/10.1039/c8cc02788a.

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