Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)-Reference-Cited by-同舟云学术

Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)

Published:2020 Issue:29 Volume:11 Page:7609-7614
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Schuhmacher Anne¹²³⁴,Shiro Tomoya¹²³⁴,Ryan Sarah J.⁵⁶⁷,Bode Jeffrey W.¹²³⁴^ORCID

Affiliation:

1. Laboratory of Organic Chemistry

2. Eidgenössische Technische Hochschule (ETH) Zurich

3. 8093 Zurich

4. Switzerland

5. Small Molecule Design and Development

6. Eli Lilly and Company Indianapolis

7. USA

Abstract

Oxidative amidation of potassium acyltrifluoroborates (KATs) and amines via trifluoroborate iminiums (TIMs) delivers amides without coupling agents. This unusual approach to amides can be applied for the late-stage modification of bioactive molecules and for solid-phase peptide synthesis.

Funder

Dainippon Sumitomo Pharma

Eli Lilly and Company

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/SC/D0SC01330G

Reference55 articles.

1. The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry and Material Science , ed. A. Greenburg , C. M. Breneman and J. S. Liebman , Wiley , New York , 2000

2. Therapeutic peptides: Historical perspectives, current development trends, and future directions

3. Amide bond formation and peptide coupling

4. Key green chemistry research areas—a perspective from pharmaceutical manufacturers

5. Evaluation of alternative solvents in common amide coupling reactions: replacement of dichloromethane and N,N-dimethylformamide

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