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Palladium‐Catalyzed Oxidative Sulfamidation: A Stereoselective Synthesis for Enesulfonamides
Author(s) -
Panda Niranjan,
Yadav Sushree Arpitabala,
Giri Santanab
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601048
Subject(s) - chemistry , stereoselectivity , palladium , catalysis , intramolecular force , oxidative addition , ligand (biochemistry) , alkyl , medicinal chemistry , solvent , total synthesis , oxidative phosphorylation , inert gas , combinatorial chemistry , organic chemistry , biochemistry , receptor
A palladium‐catalyzed protocol involving oxidative C–H sulfamidation of electron‐deficient terminal alkenes is described for the stereoselective synthesis of Z‐ enesulfonamides. The possible intramolecular hydrogen bonding between the sulfamido proton (SO 2 N–H) and the carbonyl oxygen (C=O) of the ester group provides extra stability to the resulting alkyl‐palladium complex as well as to the transition state. Notably, this reaction operates at room temperature under ligand‐free conditions and does not require any inert atmosphere or dry solvent or expensive terminal oxidant. The present protocol enables the stereoselective synthesis of Z ‐enesulfonamides from the primary sulfonamides and of E ‐enesulfonamides from N ‐substituted sulfonamides. Furthermore, the selective deallylation of sulfonamides in the presence of an N ‐benzyl group was performed under the above reaction conditions.