Dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes

被引：47

作者：

Baxter, Ryan D. ^{[1
]}

Montgomery, John ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 30期

关键词：

D O I：

10.1021/ja803774s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nickel-catalyzed coupling of aldehydes, alkynes, and dialkylsilanes results in an unusual dehydrogenative cyclocondensation process to afford five-membered silacyclic products. The process allows dialkylsilanes to serve as a silylene synthetic equivalent. A mechanistic pathway for the process involving the formation of an aldehyde/alkyne-derived nickel metallacycle followed by sequential sigma-bond metathesis processes involving the two Si-H bonds has been proposed.

引用

页码：9662 / +

页数：3

共 32 条

[1] ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2128 - 2135
[2] ASYMMETRIC CATALYSIS - PRODUCTION OF CHIRAL DIOLS BY ENANTIOSELECTIVE CATALYTIC INTRAMOLECULAR HYDROSILATION OF OLEFINS
BERGENS, SH
NOHEDA, P
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2121 - 2128
[3] New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings
Chaulagain, Mani Raj
Sormunen, Grant J.
Montgomery, John
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) : 9568 - +
[4] Formation and utility of oxasilacyclopentenes derived from functionalized alkynes
Clark, TB
Woerpel, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9522 - 9523
[5] Intramolecular anti-hydrosilylation and silicon-assisted cross-coupling: Highly regio- and stereoselective synthesis of trisubstituted homoallylic alcohols
Denmark, SE
Pan, WT
[J]. ORGANIC LETTERS, 2002, 4 (23) : 4163 - 4166
[6] Sequential ring-closing metathesis and silicon-assisted cross-coupling reactions: Stereocontrolled synthesis of highly substituted unsaturated alcohols
Denmark, SE
Yang, SM
[J]. ORGANIC LETTERS, 2001, 3 (11) : 1749 - 1752
[7] Intramolecular hydrosilylation and silicon-assisted cross-coupling: An efficient route to trisubstituted homoallylic alcohols
Denmark, SE
Pan, WT
[J]. ORGANIC LETTERS, 2001, 3 (01) : 61 - 64
[8] Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene
Driver, TG
Woerpel, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) : 9993 - 10002
[9] Development of reactions of silacyclopropanes as new methods for stereoselective organic synthesis
Franz, AK
Woerpel, KA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (11) : 813 - 820
[10] Stereospecific and regioselective reactions of silacyclopropanes with carbonyl compounds catalyzed by copper salts: Evidence for a transmetalation mechanism
Franz, AK
Woerpel, KA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) : 949 - 957

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