@article{b30cf651945d4dddb96d2d2607ffe44f,
title = "Organic chemistry: A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents",
abstract = "Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to make simple C-N (amide) bonds from carboxylic acids with loss of water can be used to make C-C bonds through coupling with dialkylzinc reagents and loss of carbon dioxide. This disconnection strategy benefits from the use of a simple, inexpensive nickel catalyst and exhibits a remarkably broad scope across a range of substrates (>70 examples).",
author = "Tian Qin and Josep Cornella and Chao Li and Malins, {Lara R.} and Edwards, {Jacob T.} and Shuhei Kawamura and Maxwell, {Brad D.} and Eastgate, {Martin D.} and Baran, {Phil S.}",
note = "Funding Information: Financial support for this work was provided by Bristol-Myers Squibb, the Catalan Government (postdoctoral fellowship to J.C.), the U.S. Department of Defense (National Defense Science and Engineering Graduate fellowship to J.T.E.), NIH (F32GM117816 postdoctoral fellowship to L.R.M.), the China Scholarship Council (postdoctoral fellowship to C.L.), and the National Institute of General Medical Sciences (GM106210). We thank D.-H. Huang and L. Pasternack for assistance with nuclear magnetic resonance spectroscopy; M. Collins for providing samples of atorvastatin, cetirizine, and pregabalin; R. Mills for experimental assistance; A. Rheingold, C. E. Moore, and M. A. Galella for x-ray crystallographic analysis; M. R. Ghadiri for providing access to preparative HPLC equipment; and K. Chen for helpful discussions. Metrical parameters for the structures of 11 and 73 are available free of charge from the Cambridge Crystallographic Data Center under reference nos. CCDC-1457710 and CCDC-1457711, respectively. Publisher Copyright: Copyright 2016 by the American Association for the Advancement of Science; all rights reserved.",
year = "2016",
month = may,
day = "13",
doi = "10.1126/science.aaf6123",
language = "English (US)",
volume = "352",
pages = "801--805",
journal = "Science",
issn = "0036-8075",
publisher = "American Association for the Advancement of Science",
number = "6287",
}