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Highly Efficient Proline Ester‐based Nickel Catalysts for Michael Addition of Thiophenols to α,β‐Enones
Author(s) -
Lee WayZen,
Chiang ChienWei,
Kulkarni Girish M.,
Kuo TingShen
Publication year - 2013
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201200386
Subject(s) - chemistry , nickel , catalysis , molecule , michael reaction , catalytic cycle , medicinal chemistry , spectroscopy , combinatorial chemistry , stereochemistry , organic chemistry , physics , quantum mechanics
Two N 3 O 2 pentadentate ligands, BMPP and BPPP, were prepared for synthesizing highly efficient nickel catalysts, [Ni(BMPP)(CH 3 CN)](ClO 4 ) 2 ( 1 ) and [Ni(BPPP)(CH 3 CN)](BPh 4 )(ClO 4 ) ( 2 ), for thia‐Michael addition of thiophenols to α,β‐enones. X‐ray structures of 1 and 2 revealed that a labile CH 3 CN molecule was bound to the nickel center of the catalysts. ESI‐MS spectroscopy indicated that thiolate replaced the bound CH 3 CN molecule and coordinated to the nickel center during the catalytic cycle.