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Bismuth‐ and Hafnium‐Catalyzed Hydroamination of Vinyl Arenes with Sulfonamides, Carbamates, and Carboxamides
Author(s) -
Qin Hongbo,
Yamagiwa Noriyuki,
Matsunaga Shigeki,
Shibasaki Masakatsu
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600284
Subject(s) - hydroamination , chemistry , catalysis , substrate (aquarium) , bismuth , combinatorial chemistry , styrene , intermolecular force , organic chemistry , polymer chemistry , medicinal chemistry , copolymer , molecule , oceanography , geology , polymer
Catalytic intermolecular hydroamination of vinyl arenes is described. Our initial investigation revealed that a Bi(OTf) 3 /[Cu(CH 3 CN) 4 ]PF 6 system previously developed for catalytic intermolecular hydroamination of 1,3‐dienes was suitable for hydroamination of a styrene with sulfonamides, but the substrate generality of this system was unsatisfactory. Several metals were screened to expand the substrate scope, and a new Hf(OTf) 4 /[Cu(CH 3 CN) 4 ]PF 6 system was determined to be highly suitable. The combination of Hf(OTf) 4 and [Cu(CH 3 CN) 4 ]PF 6 efficiently promoted the hydroamination of various vinyl arenes, including less‐reactive vinyl arenes with electron‐withdrawing groups. This strategy was applied to sulfonamides, carbamates, and carboxamides, and products were obtained in up to 99 % yield with 0.3–10 mol % catalyst loading.