Iridium(I) N‐heterocyclic carbene complexes of formula Ir(κ2O,O’‐BHetA)(IPr)(η2‐coe) [BHetA=bis‐heteroatomic acidato, acetylacetonate or acetate; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazolin‐2‐carbene; coe=cyclooctene] have been pr...
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https://www.riss.kr/link?id=O111400350
2021년
-
0947-6539
1521-3765
SCI;SCIE;SCOPUS
학술저널
11868-11878 [※수록면이 p5 이하이면, Review, Columns, Editor's Note, Abstract 등일 경우가 있습니다.]
0
상세조회0
다운로드다국어 초록 (Multilingual Abstract)
Iridium(I) N‐heterocyclic carbene complexes of formula Ir(κ2O,O’‐BHetA)(IPr)(η2‐coe) [BHetA=bis‐heteroatomic acidato, acetylacetonate or acetate; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazolin‐2‐carbene; coe=cyclooctene] have been pr...
Iridium(I) N‐heterocyclic carbene complexes of formula Ir(κ2O,O’‐BHetA)(IPr)(η2‐coe) [BHetA=bis‐heteroatomic acidato, acetylacetonate or acetate; IPr=1,3‐bis(2,6‐diisopropylphenyl)imidazolin‐2‐carbene; coe=cyclooctene] have been prepared by treating Ir(κ2O,O’‐BHetA)(η2‐coe)2 complexes with IPr. These complexes react with 2‐vinylpyridine to afford the hydrido‐iridium(III)‐alkenyl cyclometalated derivatives IrH(κ2O,O’‐BHetA)(κ2N,C‐C7H6N)(IPr) through the iridium(I) intermediate Ir(κ2O,O’‐BHetA)(IPr)(η2‐C7H7N). The cyclometalated IrH(κ2O,O’‐acac)(κ2N,C–C7H6N)(IPr) complex efficiently catalyzes the hydroalkenylation of aromatic and aliphatic terminal alkynes and enynes with 2‐vinylpyridine to afford 2‐(4R‐butadienyl)pyridines with Z,E configuration as the major reaction products (yield up to 89 %). In addition, unprecedented (Z)‐2‐butadienyl‐5R‐pyridine derivatives have been obtained as minor reaction products (yield up to 21 %) from the elusive 1Z,3gem‐butadienyl hydroalkenylation products. These compounds undergo a thermal 6π‐electrocyclization to afford bicyclic 4H‐quinolizine derivatives that, under catalytic reaction conditions, tautomerize to 6H‐quinolizine to afford the (Z)‐2‐(butadienyl)‐5R‐pyridine by a retro‐electrocyclization reaction.
Magic watchmaker. The Ir‐NHC catalyst efficiently hydroalkenylates alkynes with 2‐vinylpyridine. The interplay of the NHC and acac ligands drives the reaction via IrIII intermediates allowing the selective formation of expected and unexpected butadienylpyridine derivatives. The unusual 5‐substituted 2‐butadienylpyridines result from a complex stepwise mechanism involving quinolizine intermediates.