Boron Catalysis in the Transformation of Carboxylic Acids and Carboxylic Acid Derivatives. Issue 1 (15th December 2022)

• Record Type: Journal Article
• Authors: Sawamura, Masaya; Shimizu, Yohei
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 1(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-15
• Subjects: Amides -- Boron catalysis -- Carboxylic acids -- Chemoselectivity -- Esters; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201249
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Carboxylic acids, amides, and esters are ubiquitous motifs in functional organic molecules. However, the reactivities of these high oxidation state carbonyl compounds are far lower than ketones and aldehydes, and catalysts applicable to transform this class of carbonyl compounds are limited. On the other hand, boron catalysts have found various applications in the transformation of carbonyl compounds by taking advantage of the unique properties derived from their vacant p ‐orbitals. The continuous advancement of boron catalysis has realized several unprecedented direct transformations of carboxylic acids, amides, and esters in the past decade. In this review, representative achievements of boron catalysis are summarized according to reaction types by focusing on their applications to non‐activated carboxylic acids, amides, and esters. Abstract : Recent advances in boron catalysis with non‐activated carboxylic acids, amides, and esters are summarized. Dehydrative amidation, reduction by silane reagents, C−C bond formation at α‐position, heteroatom‐functionalization at α‐position, 1, 4‐addition, and other types of reactions are discussed with overview of mechanistic insights obtained during the past decade.