Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Reviews and Accounts
Design, Synthesis, and Application of Multiboron Heterocycle to Direct Amidation Catalyst
Hidetoshi NodaMasakatsu ShibasakiNaoya Kumagai
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2020 Volume 78 Issue 10 Pages 971-978

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Abstract

The synthesis of a multiboron heterocycle and its application to a direct amidation catalyst are described. The heterocycle comprised of B3NO2 is called DATB. The DATB-catalyzed direct amide formation is well suited for the synthesis of a wide range of amides, including previously intractable ones. The catalysis can also be applied to peptide synthesis and N-acylation of sulfoximines. The most active DATB contains four boron atoms in its structure, and the detailed mechanistic study revealed their distinctive roles in the catalytic cycle, depending on the given chemical environment. A pyrimidine containing analog was also developed and evaluated as a more readily accessible amidation catalyst than the original one. The Pym-DATB is now available from a commercial vendor. Current trends and future perspective in the boron-catalyzed direct amidation are also discussed.

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© 2020 The Society of Synthetic Organic Chemistry, Japan
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