Journal
TETRAHEDRON LETTERS
Volume 57, Issue 6, Pages 654-657Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.12.107
Keywords
Solid copper-mediated; Arylboronic acid; N-arylation; Continuous flow; C-N coupling
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Funding
- Manitoba Medical Service Foundation
- Dr. Paul H.T. Thorlakson Foundation
- College of Pharmacy at the University of Manitoba
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We have developed two general methods for the C-N cross-coupling of phenylboronic acids with amines using solid copper flow reactors, in combination with an oxidant. We have developed one method for a C-N arylation reaction which employs a solid copper coil reactor, in combination with tert-butyl peroxybenzoate, to give products in moderate isolated yields. We have also developed a general method for the C-N cross coupling of phenylboronic acids using a column packed with solid copper powder, in combination with acetic acid and TEMPO, to give products in isolated yields in excess of 75+%. We have also applied our general copper powder method to generate a library of products which highlights the utility of solid copper flow reactors for C-N cross coupling reactions, generating 16 examples in good yields. Mechanistic implications and future directions are also discussed. (C) 2016 Elsevier Ltd. All rights reserved.
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