Preferential carbene insertion into Ge-H vs. other heavier group 14 hydrides via samarium carbenoids

被引:9
作者
Kondo, Hitoshi [1 ]
Yamanoi, Yoshinori [1 ]
Nishihara, Hiroshi [1 ]
机构
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
关键词
PROMOTED CYCLOPROPANATION REACTIONS; SI-H; CARBONYL-COMPOUNDS; METAL; ESTERS; AMIDES; BOND;
D O I
10.1039/c1cc11256b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The relative reactivities of Zn, Al, and Sm carbenoids in the chemoselective carbene insertion reaction of heavier group 14 hydrides were studied. By variation of the reaction protocols using Sm carbenoids, insertion reaction can favour the Ge-H bonds to give Ge-alkylated derivatives in good to high yield.
引用
收藏
页码:6671 / 6673
页数:3
相关论文
共 41 条
[2]   SYNTHESIS OF ALPHA-(ALKOXYSILYL)ACETIC ESTERS - A ROUTE TO 1,2-DIOLS [J].
ANDREY, O ;
LANDAIS, Y ;
PLANCHENAULT, D ;
WEBER, V .
TETRAHEDRON, 1995, 51 (44) :12083-12096
[3]  
[Anonymous], 2004, METAL CARBENES ORGAN
[4]   A NEW AND GENERAL-SYNTHESIS OF ALPHA-SILYL CARBONYL-COMPOUNDS BY SI-H INSERTION FROM TRANSITION-METAL CATALYZED-REACTIONS OF DIAZO ESTERS AND DIAZO KETONES [J].
BAGHERI, V ;
DOYLE, MP ;
TAUNTON, J ;
CLAXTON, EE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6158-6160
[5]   Reaction of dihydrosilanes with ethyl diazoacetate: Synthesis of 3,3-disubstituted 3-silaglutarates [J].
Barnier, JP ;
Blanco, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 514 (1-2) :67-71
[6]   TETRANUCLEAR HETEROCYCLIC COMPLEX-DIMETHYLGERMYLDIMETHYLSILYLMETHANEDIIRON OCTACARBONYL [J].
BARRAU, J ;
BENHAMIDA, N ;
SATGE, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 387 (01) :65-76
[7]   Asymmetric rhodium carbenoid insertion into the Si-H bond [J].
Buck, RT ;
Doyle, MP ;
Drysdale, MJ ;
Ferris, L ;
Forbes, DC ;
Haigh, D ;
Moody, CJ ;
Pearson, ND ;
Zhou, QL .
TETRAHEDRON LETTERS, 1996, 37 (42) :7631-7634
[8]   Parallel synthesis techniques in the identification of new chiral dirhodium(II) carboxylates for asymmetric carbenoid insertion reactions [J].
Buck, RT ;
Coe, DM ;
Drysdale, MJ ;
Moody, CJ ;
Pearson, ND .
TETRAHEDRON LETTERS, 1998, 39 (39) :7181-7184
[9]   A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds [J].
Bulugahapitiya, P ;
Landais, Y ;
ParraRapado, L ;
Planchenault, D ;
Weber, V .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1630-1641
[10]   Reinvestigation of the chemoselective cyclopropanation of allylic alcohols, allylic ethers and alkenes: a comparison between various reagents and protocols [J].
Charette, AB ;
Beauchemin, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :702-708