Boron-Catalyzed Michael Reaction of Donor-Acceptor Carboxylic Acid Pairs Enabling Direct Synthesis of 1,5-Dicarboxylic Acids.

Org Lett

Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan.

Published: July 2024

A boron-catalyzed Michael reaction using pairs of carboxylic acids was developed. The reaction occurs through dual activation of the two substrates by a boron catalyst, which facilitates boron enolate formation from the donor carboxylic acid with simultaneous activation of the α,β-unsaturated carboxylic acid as the acceptor. α-Aryl and α-alkenyl carboxylic acids were applicable as donors. The versatility and utility of this reaction were demonstrated by the direct use of pharmaceuticals as donor carboxylic acids.

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http://dx.doi.org/10.1021/acs.orglett.4c01542DOI Listing

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