Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3- triazoles

Jeffrey C. Culhane, Valery V. Fokin

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3- triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.

Original languageEnglish
Pages (from-to)4578-4580
Number of pages3
JournalOrganic Letters
Volume13
Issue number17
DOIs
Publication statusPublished - 2 Sep 2011
Externally publishedYes

Fingerprint

Triazoles
Azides
carbenes
alkynes
rhodium
shelves
alkenes
amines
reactivity
catalysts
Rhodium
Alkynes
Alkenes
synthesis
Amines
Catalysts
carbene

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3- triazoles. / Culhane, Jeffrey C.; Fokin, Valery V.

In: Organic Letters, Vol. 13, No. 17, 02.09.2011, p. 4578-4580.

Research output: Contribution to journalArticle

Culhane, Jeffrey C. ; Fokin, Valery V. / Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3- triazoles. In: Organic Letters. 2011 ; Vol. 13, No. 17. pp. 4578-4580.
@article{69e4e70ad94d4c55932950cc2c240b16,
title = "Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3- triazoles",
abstract = "Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3- triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.",
author = "Culhane, {Jeffrey C.} and Fokin, {Valery V.}",
year = "2011",
month = "9",
day = "2",
doi = "10.1021/ol201705k",
language = "English",
volume = "13",
pages = "4578--4580",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3- triazoles

AU - Culhane, Jeffrey C.

AU - Fokin, Valery V.

PY - 2011/9/2

Y1 - 2011/9/2

N2 - Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3- triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.

AB - Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3- triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add to olefins.

UR - http://www.scopus.com/inward/record.url?scp=80052248010&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052248010&partnerID=8YFLogxK

U2 - 10.1021/ol201705k

DO - 10.1021/ol201705k

M3 - Article

VL - 13

SP - 4578

EP - 4580

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 17

ER -