Highly efficient proline ester-based nickel catalysts for Michael addition of thiophenols to α,β-enones

Way Zen Lee; Chien Wei Chiang; Girish M. Kulkarni; Ting Shen Kuo

doi:10.1002/jccs.201200386

Highly efficient proline ester-based nickel catalysts for Michael addition of thiophenols to α,β-enones

Way Zen Lee^*
, Chien Wei Chiang
, Girish M. Kulkarni
, Ting Shen Kuo

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Two N₃O₂ pentadentate ligands, BMPP and BPPP, were prepared for synthesizing highly efficient nickel catalysts, [Ni(BMPP)(CH ₃CN)](ClO₄)₂ (1) and [Ni(BPPP)(CH ₃CN)](BPh₄)(ClO₄) (2), for thia-Michael addition of thiophenols to α,β-enones. X-ray structures of 1 and 2 revealed that a labile CH3CN molecule was bound to the nickel center of the catalysts. ESI-MS spectroscopy indicated that thiolate replaced the bound CH3CN molecule and coordinated to the nickel center during the catalytic cycle.

Original language	English
Pages (from-to)	245-250
Number of pages	6
Journal	Journal of the Chinese Chemical Society
Volume	60
Issue number	3
DOIs	https://doi.org/10.1002/jccs.201200386
Publication status	Published - 2013 Mar

Keywords

Conjugate addition
Nickel complexes
Proline derivatives
Pyridine derivatives
Thia-Michael addition

ASJC Scopus subject areas

General Chemistry

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10.1002/jccs.201200386

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title = "Highly efficient proline ester-based nickel catalysts for Michael addition of thiophenols to α,β-enones",

abstract = "Two N3O2 pentadentate ligands, BMPP and BPPP, were prepared for synthesizing highly efficient nickel catalysts, [Ni(BMPP)(CH 3CN)](ClO4)2 (1) and [Ni(BPPP)(CH 3CN)](BPh4)(ClO4) (2), for thia-Michael addition of thiophenols to α,β-enones. X-ray structures of 1 and 2 revealed that a labile CH3CN molecule was bound to the nickel center of the catalysts. ESI-MS spectroscopy indicated that thiolate replaced the bound CH3CN molecule and coordinated to the nickel center during the catalytic cycle.",

keywords = "Conjugate addition, Nickel complexes, Proline derivatives, Pyridine derivatives, Thia-Michael addition",

author = "Lee, \{Way Zen\} and Chiang, \{Chien Wei\} and Kulkarni, \{Girish M.\} and Kuo, \{Ting Shen\}",

year = "2013",

month = mar,

doi = "10.1002/jccs.201200386",

language = "English",

volume = "60",

pages = "245--250",

journal = "Journal of the Chinese Chemical Society",

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publisher = "John Wiley and Sons Inc.",

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T1 - Highly efficient proline ester-based nickel catalysts for Michael addition of thiophenols to α,β-enones

AU - Lee, Way Zen

AU - Chiang, Chien Wei

AU - Kulkarni, Girish M.

AU - Kuo, Ting Shen

PY - 2013/3

Y1 - 2013/3

N2 - Two N3O2 pentadentate ligands, BMPP and BPPP, were prepared for synthesizing highly efficient nickel catalysts, [Ni(BMPP)(CH 3CN)](ClO4)2 (1) and [Ni(BPPP)(CH 3CN)](BPh4)(ClO4) (2), for thia-Michael addition of thiophenols to α,β-enones. X-ray structures of 1 and 2 revealed that a labile CH3CN molecule was bound to the nickel center of the catalysts. ESI-MS spectroscopy indicated that thiolate replaced the bound CH3CN molecule and coordinated to the nickel center during the catalytic cycle.

AB - Two N3O2 pentadentate ligands, BMPP and BPPP, were prepared for synthesizing highly efficient nickel catalysts, [Ni(BMPP)(CH 3CN)](ClO4)2 (1) and [Ni(BPPP)(CH 3CN)](BPh4)(ClO4) (2), for thia-Michael addition of thiophenols to α,β-enones. X-ray structures of 1 and 2 revealed that a labile CH3CN molecule was bound to the nickel center of the catalysts. ESI-MS spectroscopy indicated that thiolate replaced the bound CH3CN molecule and coordinated to the nickel center during the catalytic cycle.

KW - Conjugate addition

KW - Nickel complexes

KW - Proline derivatives

KW - Pyridine derivatives

KW - Thia-Michael addition

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U2 - 10.1002/jccs.201200386

DO - 10.1002/jccs.201200386

M3 - Article

AN - SCOPUS:84878274457

SN - 0009-4536

VL - 60

SP - 245

EP - 250

JO - Journal of the Chinese Chemical Society

JF - Journal of the Chinese Chemical Society

IS - 3

ER -

Highly efficient proline ester-based nickel catalysts for Michael addition of thiophenols to α,β-enones

Abstract

Keywords

ASJC Scopus subject areas

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