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
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
收藏
页码:9662 / +
页数:3
相关论文
共 32 条
[1]   ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION [J].
BERGENS, SH ;
NOHEDA, P ;
WHELAN, J ;
BOSNICH, B .
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 [J].
BERGENS, SH ;
NOHEDA, P ;
WHELAN, J ;
BOSNICH, B .
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 [J].
Chaulagain, Mani Raj ;
Sormunen, Grant J. ;
Montgomery, John .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) :9568-+
[4]   Formation and utility of oxasilacyclopentenes derived from functionalized alkynes [J].
Clark, TB ;
Woerpel, KA .
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 [J].
Denmark, SE ;
Pan, WT .
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 [J].
Denmark, SE ;
Yang, SM .
ORGANIC LETTERS, 2001, 3 (11) :1749-1752
[7]   Intramolecular hydrosilylation and silicon-assisted cross-coupling: An efficient route to trisubstituted homoallylic alcohols [J].
Denmark, SE ;
Pan, WT .
ORGANIC LETTERS, 2001, 3 (01) :61-64
[8]   Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene [J].
Driver, TG ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9993-10002
[9]   Development of reactions of silacyclopropanes as new methods for stereoselective organic synthesis [J].
Franz, AK ;
Woerpel, KA .
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 [J].
Franz, AK ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :949-957