4.4 Article

One-pot carbonyl reduction and carbonate formation using sodium borohydride in dialkyl carbonate solvents

Journal

TETRAHEDRON LETTERS
Volume 60, Issue 44, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2019.151203

Keywords

Carbonate formation; One-pot synthesis; Mixed carbonates; Tandem reactions

Funding

  1. M. J. Murdock Charitable Trust, Vancouver, WA [2014120:MNL]

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Preparation of mixed carbonates proceeded in one step from ketones and aldehydes via treatment with NaBH4 in dimethyl or diethyl carbonate solvent at elevated temperatures. This is an efficient and convenient alternative to the traditional two-step sequence of carbonyl reduction to alcohol and subsequent carbonate formation by treatment with an alkyl chloroformate. 25 examples are presented from 49 to 92% yield, highlighting the versatility of this reaction. Crown Copyright (C) 2019 Published by Elsevier Ltd. All rights reserved.

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