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  1. Home
  2. Indian Institute of Technology Madras
  3. Publication2
  4. Ruthenium(II)-Catalyzed Regioselective C-H Olefination of Aromatic Ketones and Amides with Allyl Sulfones
 
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Ruthenium(II)-Catalyzed Regioselective C-H Olefination of Aromatic Ketones and Amides with Allyl Sulfones

Date Issued
03-09-2021
Author(s)
Dana, Suman
Giri, Chandan Kumar
Md Mahiuddin Baidya 
Indian Institute of Technology, Madras
DOI
10.1021/acs.orglett.1c02424
Abstract
A Ru(II)-catalyzed cross-dehydrogenative Heck-type olefination of arenes with allyl sulfones leveraging the assistance of weakly coordinating ketone and amide functional groups is reported. It features a distinct reactivity profile in comparison to other allylic congeners, where β-sulfonyl elimination was not detected. The ambiphilic nature of the allyl sulfone side chain has also been demonstrated through intramolecular aza-Michael addition and aldol condensation. Mechanistic studies indicated the involvement of a reversible metalation step, where β-hydride elimination takes place selectively from the benzylic position.
Volume
23
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