Formation of an aza-nickelacycle by reaction of an imine and an alkyne with nickel(0): Oxidative cyclization, insertion, and reductive elimination

被引：85

作者：

Ogoshi, Sensuke ^{[1
]}

Ikeda, Haruo ^{[1
]}

Kurosawa, Hideo ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 26期

关键词：

alkynes; cycloaddition; imines; metallacycles; nickel;

D O I：

10.1002/anie.200700688

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Cyclize, add, reduce: The oxidative cyclization of an imine and an alkyne with nickel(0) followed by the insertion of a second alkyne gives a seven-membered aza-nickelacycle (see scheme). Subsequent reductive elimination yields a 1,2-dihydropyridine. This sequential reaction process is expanded to a one-step nickel-catalyzed [2+2+2] cycloaddition of two alkynes and an imine. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4930 / 4932

页数：3

共 23 条

[1] Organometallic chemistry of amidate complexes.: Accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II)
Fujita, Ken-ichi
Yamashita, Makoto
Puschmann, Florian
Alvarez-Falcon, Miguel Martinez
Incarvito, Christopher D.
Hartwig, John F.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) : 9044 - 9045
[2] HOBERG H, 1979, SYNTHESIS-STUTTGART, P525
[3] MODEL COMPLEX OF NICKEL FOR THE C-C BONDING OF ALKYNES WITH ISOCYANATES
HOBERG, H
OSTER, BW
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 234 (02) : C35 - C38
[4] NICKEL COMPOUNDS AS INTERMEDIATE COMPLEXES OF [2+2+2']-CYCLOADDITION OF ALKYNES WITH ISOCYANATES OF 2-PYRIDONES
HOBERG, H
OSTER, BW
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 252 (03) : 359 - 364
[5] Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes
Huang, WS
Chan, J
Jamison, TF
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4221 - 4223
[6] Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes
Mahandru, GM
Liu, G
Montgomery, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3698 - 3699
[7] Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes
Miller, KM
Jamison, TF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) : 15342 - 15343
[8] Catalytic asymmetric reductive coupling of alkynes and aldehydes:: Enantioselective synthesis of allylic alcohols and α-hydroxy ketones
Miller, KM
Huang, WS
Jamison, TF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3442 - 3443
[9] Eight-membered ring construction by [4+2+2] annulation involving β-carbon elimination
Murakami, M
Ashida, S
Matsuda, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) : 2166 - 2167
[10] Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones
Murakami, M
Ashida, S
Matsuda, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) : 6932 - 6933

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