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The N ‐Alkylation of Sulfonamides with Alcohols in Water Catalyzed by the Water‐Soluble Iridium Complex {Cp*Ir[6,6′‐(OH) 2 bpy](H 2 O)}[OTf] 2
Author(s) -
Qu Panpan,
Sun Chunlou,
Ma Juan,
Li Feng
Publication year - 2014
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.201300711
Subject(s) - iridium , chemistry , bifunctional , ligand (biochemistry) , alkylation , catalysis , nucleophile , chelation , medicinal chemistry , combinatorial chemistry , inorganic chemistry , organic chemistry , biochemistry , receptor
The water‐soluble iridium complex {Cp*Ir[6,6′‐(OH) 2 bpy](H 2 O)}[OTf] 2 (Cp*= η 5 ‐pentamethylcyclopentadienyl, bpy=2,2′‐bipyridine) was found to be a general and highly efficient catalyst for the N ‐alkylation of the poor nucleophilic sulfonamides with alcohols as alkylating agents in water. The presence of OH units in the bpy ligand is crucially important for the catalytic activity of the iridium complex. Mechanistic investigations revealed that the catalytically active species is a ligand‐metal bifunctional iridium complex bearing an N,N′ ‐chelated 2,2′‐bipyridinated ligand and an aqua ligand. Notably, the present catalytic system and the proposed mechanism provide a new horizon and scope for the development of “hydrogen autotransfer (or hydrogen‐borrowing) processes”.