4.4 Article

Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone

Journal

TETRAHEDRON LETTERS
Volume 56, Issue 50, Pages 7008-7011

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.11.002

Keywords

C-C cleavage; alpha-Nitroketone; Bromamine-T; Esters; Amide

Funding

  1. Department of Science and Technology (DST), India [SR/S1/OC-43/2011]

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A catalyst free protocol has been developed for nucleophilic C-sp2 C-sp3 bond cleavage of alpha-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted alpha-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

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