The reaction of thio acids with azides: A new mechanism and new synthetic applications

Ning Shangguan, Sreenivas Katukojvala, Rachel Greenberg, Lawrence Williams

Research output: Contribution to journalArticle

255 Citations (Scopus)

Abstract

A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.

Original languageEnglish (US)
Pages (from-to)7754-7755
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number26
DOIs
StatePublished - Jul 2 2003

Fingerprint

Azides
Amides
Acids
Amines
Water
Substrates

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Shangguan, Ning ; Katukojvala, Sreenivas ; Greenberg, Rachel ; Williams, Lawrence. / The reaction of thio acids with azides : A new mechanism and new synthetic applications. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 26. pp. 7754-7755.
@article{32a31fb2d6e244e3bf0f292363dfc5d8,
title = "The reaction of thio acids with azides: A new mechanism and new synthetic applications",
abstract = "A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.",
author = "Ning Shangguan and Sreenivas Katukojvala and Rachel Greenberg and Lawrence Williams",
year = "2003",
month = "7",
day = "2",
doi = "10.1021/ja0294919",
language = "English (US)",
volume = "125",
pages = "7754--7755",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "26",

}

The reaction of thio acids with azides : A new mechanism and new synthetic applications. / Shangguan, Ning; Katukojvala, Sreenivas; Greenberg, Rachel; Williams, Lawrence.

In: Journal of the American Chemical Society, Vol. 125, No. 26, 02.07.2003, p. 7754-7755.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The reaction of thio acids with azides

T2 - A new mechanism and new synthetic applications

AU - Shangguan, Ning

AU - Katukojvala, Sreenivas

AU - Greenberg, Rachel

AU - Williams, Lawrence

PY - 2003/7/2

Y1 - 2003/7/2

N2 - A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.

AB - A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.

UR - http://www.scopus.com/inward/record.url?scp=0038788894&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0038788894&partnerID=8YFLogxK

U2 - 10.1021/ja0294919

DO - 10.1021/ja0294919

M3 - Article

C2 - 12822965

AN - SCOPUS:0038788894

VL - 125

SP - 7754

EP - 7755

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 26

ER -