Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones

Pelter, Andrew, Smith, Keith ORCID: https://orcid.org/0000-0003-4838-5651, Elgendy, Said M. A. and Rowlands, Martin 1993. Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones. Tetrahedron 49 (32) , pp. 7104-7118. 10.1016/S0040-4020(01)87982-5

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Abstract

The condensation of boron stabilised carbanions, Mes2BCHLiR1, (R1≠H) with aliphatic aldehydes, R2CHO, followed by treatment with trifluoroacetic anhydride (TFAA) or N-chlorosuccinimide (NCS) is an unique, broadly applicable redox process that yields ketones, R1CH2COR2, directly and in high yields. The anion Mes2BCH2Li (Mes2BCHLiR1, R1H) gives high yields of alkenes, R2CHCH2 in the same conditions.

Item Type:	Article
Status:	Published
Schools:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Pergamon Press
ISSN:	0040-4020
Last Modified:	04 Jun 2017 02:51
URI:	https://orca.cardiff.ac.uk/id/eprint/12672

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