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

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 23期

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

页码：6671 / 6673

页数：3

共 41 条

[11] Sequential elimination-cyclopropanation reactions promoted by samarium:: Highly diastereoselective synthesis of cyclopropylamides [J].

Concellón, JM ;

Rodríguez-Solla, H ;

Llavona, R .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :1132-1133

[12]

Concellón JM, 2002, ANGEW CHEM INT EDIT, V41, P1917, DOI 10.1002/1521-3773(20020603)41:11<1917::AID-ANIE1917>3.0.CO

[13]

2-1

[14] The first cyclopropanation reaction of unmasked α,β-unsaturated carboxylic acids:: Direct and complete stereospecific synthesis of cyclopropanecarboxylic acids promoted by Sm/CHI3 [J].

Concellon, Jose M. ;

Rodriguez-Solla, Humberto ;

Simal, Carmen .

ORGANIC LETTERS, 2007, 9 (14) :2685-2688

[15] Speciation and mechanistic studies of chiral copper(I) Schiff base precursors mediating asymmetric carbenoid insertion reactions of diazoacetates into the Si-H bond of silanes [J].

Dakin, LA ;

Ong, PC ;

Panek, JS ;

Staples, RJ ;

Stavropoulos, P .

ORGANOMETALLICS, 2000, 19 (15) :2896-2908

[16] Rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed asymmetric insertions of vinyl- and phenylcarbenoids into the Si-H bond [J].

Davies, HML ;

Hansen, T ;

Rutberg, J ;

Bruzinski, PR .

TETRAHEDRON LETTERS, 1997, 38 (10) :1741-1744

[17] Theoretical studies on reaction pathways of Samarium(II) carbenoid-promoteded cyclopropanation reaction of ethylene [J].

Geng, ZY ;

Zhang, XH ;

Wang, YC ;

Fang, R ;

Gao, LG ;

Chen, XX ;

Zhao, CY .

CHINESE JOURNAL OF CHEMICAL PHYSICS, 2006, 19 (01) :69-75

[18] REACTIONS OF CARBONYL-COMPOUNDS WITH BENZYL CHLOROMETHYL ETHER OF DIIODOMETHANE IN THE PRESENCE OF SAMARIUM(II) IODIDE OR METALLIC SAMARIUM - NEW ROUTES TO 1,2-DIOLS, IODOHYDRINS AND CYCLOPROPANOLS [J].

IMAMOTO, T ;

HATAJIMA, T ;

TAKIYAMA, N ;

TAKEYAMA, T ;

KAMIYA, Y ;

YOSHIZAWA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3127-3135

[19] DIVALENT SAMARIUM-INDUCED CYCLOPROPANATION OF LITHIUM ENOLATES - A ONE-POT SYNTHESIS OF CYCLOPROPANOLS FROM KETONES [J].

IMAMOTO, T ;

TAKIYAMA, N .

TETRAHEDRON LETTERS, 1987, 28 (12) :1307-1308

[20] Methylene insertion reactions of samarium carbenoids into boron-hydrogen and phosphorus-hydrogen bonds [J].

Imamoto, T ;

Yamanoi, Y .

CHEMISTRY LETTERS, 1996, (08) :705-706

← 1 2 3 4 5 →