Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene derivatives for C(sp3)-C(sp) bond formation catalyzed by a B12 complex.

作者: Li Chen , Yohei Kametani , Kenji Imamura , Tsukasa Abe , Yoshihito Shiota

DOI: 10.1039/C9CC06185A

关键词:

摘要: Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene and its derivatives catalyzed by the cobalamin derivative (B12) [Ir(dtbbpy)(ppy)2]PF6 photocatalyst at room temperature are reported. The robust B12 catalyst Ir provided high turnover numbers over 33 000 for reactions.

参考文章(27)
Wenbo Liu, Lu Li, Chao-Jun Li, Empowering a transition-metal-free coupling between alkyne and alkyl iodide with light in water Nature Communications. ,vol. 6, pp. 6526- 6526 ,(2015) , 10.1038/NCOMMS7526
Kenkichi Sonogashira, Development of Pd–Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides Journal of Organometallic Chemistry. ,vol. 653, pp. 46- 49 ,(2002) , 10.1016/S0022-328X(02)01158-0
Rafael Chinchilla, Carmen Nájera, Recent advances in Sonogashira reactions Chemical Society Reviews. ,vol. 40, pp. 5084- 5121 ,(2011) , 10.1039/C1CS15071E
Karl Gruber, Barbara Puffer, Bernhard Kräutler, Vitamin B12-derivatives—enzyme cofactors and ligands of proteins and nucleic acids Chemical Society Reviews. ,vol. 40, pp. 4346- 4363 ,(2011) , 10.1039/C1CS15118E
Ei-ichi Negishi, Luigi Anastasia, Palladium-catalyzed alkynylation. Chemical Reviews. ,vol. 103, pp. 1979- 2017 ,(2003) , 10.1021/CR020377I
Yumeng Xi, Hong Yi, Aiwen Lei, Synthetic applications of photoredox catalysis with visible light Organic and Biomolecular Chemistry. ,vol. 11, pp. 2387- 2403 ,(2013) , 10.1039/C3OB40137E
Wenbo Liu, Zhengwang Chen, Lu Li, Haining Wang, Chao-Jun Li, Transition-Metal-Free Coupling of Alkynes with α-Bromo Carbonyl Compounds: An Efficient Approach towards β,γ-Alkynoates and Allenoates Chemistry: A European Journal. ,vol. 22, pp. 5888- 5893 ,(2016) , 10.1002/CHEM.201600219
Kazimer L. Skubi, Travis R. Blum, Tehshik P. Yoon, Dual Catalysis Strategies in Photochemical Synthesis Chemical Reviews. ,vol. 116, pp. 10035- 10074 ,(2016) , 10.1021/ACS.CHEMREV.6B00018
Nathan A. Romero, David A. Nicewicz, Organic Photoredox Catalysis Chemical Reviews. ,vol. 116, pp. 10075- 10166 ,(2016) , 10.1021/ACS.CHEMREV.6B00057
Daryl Staveness, Irene Bosque, Corey R. J. Stephenson, Free Radical Chemistry Enabled by Visible Light-Induced Electron Transfer Accounts of Chemical Research. ,vol. 49, pp. 2295- 2306 ,(2016) , 10.1021/ACS.ACCOUNTS.6B00270