Sulfonyl azides as precursors in ligand-free palladium-catalyzed synthesis of sulfonyl carbamates and sulfonyl ureas and synthesis of sulfonamides

Shiao Y. Chow; Marc Y. Stevens; Luke R. Odell

doi:10.1021/acs.joc.5b02755

Sulfonyl azides as precursors in ligand-free palladium-catalyzed synthesis of sulfonyl carbamates and sulfonyl ureas and synthesis of sulfonamides

Shiao Y. Chow, Marc Y. Stevens, Luke R. Odell^*

^*Corresponding author for this work

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl₂, and CO gas, released ex situ from Mo(CO)₆, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.

Original language	English
Pages (from-to)	2681-2691
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	81
Issue number	7
DOIs	https://doi.org/10.1021/acs.joc.5b02755
Publication status	Published - 11 Mar 2016

Funding

The authors thank Prof. Adolf Gogoll for assistance with 15N NMR studies, and Dr. Lisa Haigh for assistance with accurate mass determination. Financial support from the Knut and Alice Wallenberg foundation and the Carl Tryggers Stiftelse för Vetenskaplig Forskning (CTS) is gratefully acknowledged.

Keywords

amines
azides
organic compounds
sulfones
urea

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10.1021/acs.joc.5b02755

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abstract = "An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)6, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.",

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T1 - Sulfonyl azides as precursors in ligand-free palladium-catalyzed synthesis of sulfonyl carbamates and sulfonyl ureas and synthesis of sulfonamides

AU - Chow, Shiao Y.

AU - Stevens, Marc Y.

AU - Odell, Luke R.

PY - 2016/3/11

Y1 - 2016/3/11

N2 - An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)6, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.

AB - An efficient synthesis of sulfonyl carbamates and sulfonyl ureas from sulfonyl azides employing a palladium-catalyzed carbonylation protocol has been developed. Using a two-chamber system, sulfonyl azides, PdCl2, and CO gas, released ex situ from Mo(CO)6, were assembled to generate sulfonyl isocyanates in situ, and alcohols and aryl amines were exploited as nucleophiles to afford a broad range of sulfonyl carbamates and sulfonyl ureas. A protocol for the direct formation of substituted sulfonamides from sulfonyl azides and amines via nucleophilic substitution was also developed.

KW - amines

KW - azides

KW - organic compounds

KW - sulfones

KW - urea

U2 - 10.1021/acs.joc.5b02755

DO - 10.1021/acs.joc.5b02755

M3 - Article

SN - 0022-3263

VL - 81

SP - 2681

EP - 2691

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Sulfonyl azides as precursors in ligand-free palladium-catalyzed synthesis of sulfonyl carbamates and sulfonyl ureas and synthesis of sulfonamides

Abstract

Funding

Keywords

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