Ruthenium(II)-Catalyzed Oxidative CH Alkenylations of Sulfonic Acids, Sulfonyl Chlorides and Sulfonamides

Ruthenium(II)-Catalyzed Oxidative CH Alkenylations of Sulfonic Acids, Sulfonyl Chlorides and Sulfonamides

Twofold CH functionalization of aromatic sulfonic acids was achieved with an insitu generated ruthenium(II) catalyst. The optimized cross-dehydrogenative alkenylation protocol proved applicable to differently substituted arenes and a variety of alkenes, including vinyl arenes, sulfones, nitriles and...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal Vol. 20; no. 46; p. 15248
Main Authors: Ma, Wenbo, Mei, Ruhuai, Tenti, Giammarco, Ackermann, Lutz
Format: Journal Article
Language:English
Published: Weinheim Wiley Subscription Services, Inc 10-11-2014
Subjects:
Acids
Chemistry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Twofold CH functionalization of aromatic sulfonic acids was achieved with an insitu generated ruthenium(II) catalyst. The optimized cross-dehydrogenative alkenylation protocol proved applicable to differently substituted arenes and a variety of alkenes, including vinyl arenes, sulfones, nitriles and ketones. The robustness of the ruthenium(II) catalyst was demonstrated by the chemoselective oxidative olefination of sulfonamides as well as sulfonyl chlorides. Mechanistic studies provided support for a reversible, acetate-assisted CH ruthenation, along with a subsequent olefin insertion.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201404604