Visible-Light-Promoted C–H Arylation by Merging Palladium Catalysis with Organic Photoredox Catalysis

作者: Jian Jiang , Wen-Man Zhang , Jian-Jun Dai , Jun Xu , Hua-Jian Xu

DOI: 10.1021/ACS.JOC.7B00140

关键词:

摘要: The use of a dual palladium/organic photoredox catalytic system enables the directed arylation arenes with aryldiazonium salts broad substrate scope at room temperature under mild reaction conditions. This study thus serves as not only an alternative route for biaryl motifs but also new example application organic catalyst.

参考文章(73)
Adrian Tlahuext-Aca, Matthew N. Hopkinson, Basudev Sahoo, Frank Glorius, Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts Chemical Science. ,vol. 7, pp. 89- 93 ,(2016) , 10.1039/C5SC02583D
Jack A. Terrett, James D. Cuthbertson, Valerie W. Shurtleff, David W. C. MacMillan, Switching on elusive organometallic mechanisms with photoredox catalysis Nature. ,vol. 524, pp. 330- 334 ,(2015) , 10.1038/NATURE14875
Xiao Yun Chen, Rebekka Anna Bohmann, Long Wang, Shunxi Dong, Christoph Räuber, Carsten Bolm, Palladium/Copper‐Cocatalyzed Oxidative Amidobrominations of Alkenes Chemistry: A European Journal. ,vol. 21, pp. 10330- 10333 ,(2015) , 10.1002/CHEM.201501629
Megan A. Cismesia, Tehshik P. Yoon, Characterizing chain processes in visible light photoredox catalysis Chemical Science. ,vol. 6, pp. 5426- 5434 ,(2015) , 10.1039/C5SC02185E
Ranjan Jana, Tejas P. Pathak, Matthew S. Sigman, Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chemical Reviews. ,vol. 111, pp. 1417- 1492 ,(2011) , 10.1021/CR100327P
Joanna Wencel-Delord, Corinna Nimphius, Honggen Wang, Frank Glorius, Rhodium(III) and Hexabromobenzene—A Catalyst System for the Cross‐Dehydrogenative Coupling of Simple Arenes and Heterocycles with Arenes Bearing Directing Groups Angewandte Chemie. ,vol. 51, pp. 13001- 13005 ,(2012) , 10.1002/ANIE.201205734
Jonathan Hubrich, Thomas Himmler, Lars Rodefeld, Lutz Ackermann, Ruthenium(II)‐Catalyzed CH Arylation of Anilides with Boronic Acids, Borinic Acids and Potassium Trifluoroborates Advanced Synthesis & Catalysis. ,vol. 357, pp. 474- 480 ,(2015) , 10.1002/ADSC.201400906
Michal Majek, Fabiana Filace, Axel Jacobi von Wangelin, On the mechanism of photocatalytic reactions with eosin Y Beilstein Journal of Organic Chemistry. ,vol. 10, pp. 981- 989 ,(2014) , 10.3762/BJOC.10.97
Gabriel Schäfer, Coraline Matthey, Jeffrey W. Bode, Facile synthesis of sterically hindered and electron-deficient secondary amides from isocyanates. Angewandte Chemie. ,vol. 51, pp. 9173- 9175 ,(2012) , 10.1002/ANIE.201204481
Irina P. Beletskaya, Valentine P. Ananikov, Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions Chemical Reviews. ,vol. 111, pp. 1596- 1636 ,(2011) , 10.1021/CR100347K