@article{87dee297bdde4b91b53cae6bba8b08dc,
title = "Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids",
abstract = "A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2⋅6 H2O—$9.5 mol−1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.",
keywords = "Suzuki cross-coupling, decarboxylation, homogeneous catalysis, nickel catalysts, redox-active esters",
author = "Jie Wang and Tian Qin and Chen, {Tie Gen} and Laurin Wimmer and Edwards, {Jacob T.} and Josep Cornella and Benjamin Vokits and Shaw, {Scott A.} and Baran, {Phil S.}",
note = "Funding Information: Financial support for this work was provided by NIH (grant number GM-097444), Bristol-Myers Squibb, the Shanghai Institute of Organic Chemistry, Zhejiang Medicine Co., and Pharmaron (postdoctoral fellowship for J.W.), Austrian Science Fund (FWF, Schr{\"o}dinger Fellowship to L. W.), Department of Defense (NDSEG fellowship to J. T. E.) and Catalan Government (Beatriu de Pinos Postdoctoral Fellowship to J.C.). We thank David E. Hill for help in HPLC measurements. We also thank Ke Chen, Michael Schmidt, and Martin D. Eastgate for helpful discussions. We are grateful to D.-H. Huang and L. Pasternack (The Scripps Research Institute) for assistance with nuclear magnetic resonance (NMR) spectroscopy. We also thank A. L. Rheingold, C. E. Moore, and M. A. Galella for X-ray crystallographic analysis. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2016",
month = aug,
day = "8",
doi = "10.1002/anie.201605463",
language = "English (US)",
volume = "55",
pages = "9676--9679",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "33",
}