Aryl Ketones as Single-Electron-Transfer Photoredox Catalysts in the Nickel-Catalyzed Homocoupling of Aryl Halides
作者： Yusuke Masuda , Naoki Ishida , Masahiro Murakami
关键词:
摘要: An intriguing photoredox system for the homocoupling of aryl halides is reported wherein thioxanthone catalyzes a single-electron transfer from an amine reductant to nickel.
sci-hub.se 参考文章(61)
L. S. Hegedus, L. L. Miller, Reaction of .pi.-allylnickel bromide complexes with organic halides. Stereochemistry and mechanism Journal of the American Chemical Society. ,vol. 97, pp. 459- 460 ,(1975) , 10.1021/JA00835A061
Elson Santiago de Alvarenga, John Mann, Photocatalysed addition of pyrrolidines to butenolides: a concise synthesis of the pyrrolizidine alkaloid ring system Journal of the Chemical Society, Perkin Transactions 1. pp. 2141- 2142 ,(1993) , 10.1039/P19930002141
T. T. Tsou, J. K. Kochi, Mechanism of biaryl synthesis with nickel complexes Journal of the American Chemical Society. ,vol. 101, pp. 7547- 7560 ,(1979) , 10.1021/JA00519A015
Durga Prasad Hari, Burkhard König, Die photokatalytische Meerwein‐Arylierung: eine klassische Aryldiazoniumsalz‐Reaktion in neuem Licht Angewandte Chemie. ,vol. 125, pp. 4832- 4842 ,(2013) , 10.1002/ANGE.201210276
Takakazu Yamamoto, Shoichiro Wakabayashi, Kohtaro Osakada, Mechanism of CC coupling reactions of aromatic halides, promoted by Ni(COD)2 in the presence of 2,2′-bipyridine and PPh3, to give biaryls Journal of Organometallic Chemistry. ,vol. 428, pp. 223- 237 ,(1992) , 10.1016/0022-328X(92)83232-7
Jagan M. R. Narayanam, Joseph W. Tucker, Corey R. J. Stephenson, Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction. Journal of the American Chemical Society. ,vol. 131, pp. 8756- 8757 ,(2009) , 10.1021/JA9033582
Z. Zuo, D. T. Ahneman, L. Chu, J. A. Terrett, A. G. Doyle, D. W. C. MacMillan, Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides Science. ,vol. 345, pp. 437- 440 ,(2014) , 10.1126/SCIENCE.1255525
Yuan L. Chow, Gonzalo E. Buono-Core, Carolyn W. B. Lee, J. C. Scaiano, Sensitized photoreduction of bis(acetylacetonato)nickel(II) by triplet-state aromatic ketones. Journal of the American Chemical Society. ,vol. 108, pp. 7620- 7627 ,(1986) , 10.1021/JA00284A027
Michael A. Ischay, Mary E. Anzovino, Juana Du, Tehshik P. Yoon, Efficient visible light photocatalysis of [2+2] enone cycloadditions. Journal of the American Chemical Society. ,vol. 130, pp. 12886- 12887 ,(2008) , 10.1021/JA805387F
Samuel Bertrand, Norbert Hoffmann, Stéphane Humbel, Jean Pierre Pete, Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET). Journal of Organic Chemistry. ,vol. 65, pp. 8690- 8703 ,(2000) , 10.1021/JO001166L