Copper-Catalyzed Alkylation of Sulfonamides with Alcohols

Water is the only by‐product in an efficient and atom‐economical Cu(OAc)2‐catalyzed coupling of alcohols with sulfonamides (see proposed mechanism; Ts= p‐toluenesulfonyl). It was discovered that bissulfonylated amidines formed as intermediates when the transhydrogenative CN bond‐forming reaction is...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 32; pp. 5912 - 5915
Main Authors Shi, Feng, Tse, Man Kin, Cui, Xinjiang, Gördes, Dirk, Michalik, Dirk, Thurow, Kerstin, Deng, Youquan, Beller, Matthias
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
Alcohols - chemistry
Alkylation
amidines
Catalysis
Chemistry
Chemistry, Multidisciplinary
copper
Copper - chemistry
CN bond formation
hydrogen borrowing
Physical Sciences
Science & Technology
sulfonamides
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
sustainable chemistry
amidines
C-N bond formation
BORROWING HYDROGEN
TERTIARY-AMINES
EFFICIENT SYNTHESIS
SECONDARY
AMIDATION
sulfonamides
HYDROAMINATION
hydrogen borrowing
BENZYL ALCOHOLS
DIRECT AMINATION
copper
N-ALKYLATION
sustainable chemistry
SELECTIVE SYNTHESIS
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Summary:Water is the only by‐product in an efficient and atom‐economical Cu(OAc)2‐catalyzed coupling of alcohols with sulfonamides (see proposed mechanism; Ts= p‐toluenesulfonyl). It was discovered that bissulfonylated amidines formed as intermediates when the transhydrogenative CN bond‐forming reaction is carried out in air act as novel ligands to stabilize the catalyst.
Bibliography:http://dx.doi.org/10.1002/anie.200901510
This research was supported by the Chinese Academy of Sciences, the DFG (SPP 1118 and Leibniz Prize), and the BMBF. F. Shi thanks the Alexander‐von‐Humboldt‐Stiftung for an AvH Fellowship.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200901510