Lithium tri-tert-butylzincate as a chemoselective metallating reagent for functionalized organic halides

被引:42
作者
Kondo, Y
Fujinami, M
Uchiyama, M
Sakamoto, T
机构
[1] Faculty of Pharmaceutical Sciences, Tohoku University, Aobayama, Aoba-ku
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 06期
关键词
D O I
10.1039/a608294g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chemoselective metallation of functionalized organic halides has been performed under mild reaction conditions using a halogen-zinc exchange with lithium tri-tert-butylzincate and subsequent transformation of the zincates has been investigated.
引用
收藏
页码:799 / 800
页数:2
相关论文
共 28 条
[1]   STEREOSELECTIVE CARBON-CARBON BOND-FORMING REACTION OF 1,1-DIBROMOCYCLOPROPANES VIA 1-HALOCYCLOPROPYLZINCATES [J].
HARADA, T ;
KATSUHIRA, T ;
HATTORI, K ;
OKU, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :2958-2965
[2]   REACTIONS OF 1,1-DIHALOALKENES WITH TRIORGANOZINCATES - A NOVEL METHOD FOR THE PREPARATION OF ALKENYLZINC SPECIES ASSOCIATED WITH CARBON-CARBON BOND FORMATION [J].
HARADA, T ;
KATSUHIRA, T ;
HARA, D ;
KOTANI, Y ;
MAEJIMA, K ;
KAJI, R ;
OKU, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4897-4907
[3]   STEREOCHEMISTRY IN CARBENOID FORMATION BY BROMINE LITHIUM AND BROMINE ZINC EXCHANGE-REACTIONS OF 1,1-DIBROMOALKENES - HIGHER REACTIVITY OF THE STERICALLY MORE HINDERED BROMINE ATOM [J].
HARADA, T ;
KATSUHIRA, T ;
OKU, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5805-5807
[4]   TRIALKYLZINCLITHIUM [R3ZNLI] - NEW REAGENT FOR CONJUGATE ADDITION TO ALPHA,BETA-UNSATURATED KETONES [J].
ISOBE, M ;
KONDO, S ;
NAGASAWA, N ;
GOTO, T .
CHEMISTRY LETTERS, 1977, (06) :679-682
[5]   CONJUGATE ADDITIONS OF GRIGNARD-REAGENTS TO ALPHA,BETA-UNSATURATED KETONES MEDIATED BY DIAMINE ZINC(II)MONOALKOXIDES [J].
JANSEN, JFGA ;
FERINGA, BL .
TETRAHEDRON LETTERS, 1988, 29 (29) :3593-3596
[6]   REGIOSELECTIVE 1,4-ADDITION TO ALPHA,BETA-UNSATURATED KETONES WITH GRIGNARD-REAGENTS MEDIATED BY (N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE)ZINC(II) CHLORIDE [J].
KJONAAS, RA ;
VAWTER, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (21) :3993-3996
[7]   REGIOSPECIFIC 1,4-ADDITION WITH GRIGNARD-DERIVED MIXED TRIORGANOZINCATE REAGENTS [J].
KJONAAS, RA ;
HOFFER, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4133-4135
[8]   PREPARATION OF ALKYLZINC BROMIDES USING A NEW MN/CU CATALYZED BROMINE-ZINC EXCHANGE-REACTION [J].
KLEMENT, I ;
KNOCHEL, P ;
CHAU, K ;
CAHIEZ, G .
TETRAHEDRON LETTERS, 1994, 35 (08) :1177-1180
[9]   PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].
KNOCHEL, P ;
SINGER, RD .
CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188
[10]   NEW APPROACH TO BORON-STABILIZED ORGANOMETALLICS [J].
KNOCHEL, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7431-7433