Zn(tmp)2:: A versatile base for the selective functionalization of C-H bonds

被引：56

作者：

Hlavinka, Mark L. ^{[1
]}

Hagadorn, John R. ^{[1
]}

机构：

[1] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA

来源：

ORGANOMETALLICS | 2007年 / 26卷 / 17期

关键词：

D O I：

10.1021/om700475t

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Zn(tMP)(2) (tMP = 2,2,6,6-tetramethylpiperidinyl anion) is an effective base for the mild deprotonation of a broad range of substrates. Functionalized organozincs thus prepared are conveniently coupled with aryl bromides using typical Pd-catalyzed coupling methods.

引用

页码：4105 / 4108

页数：4

共 35 条

[21] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].

KNOCHEL, P ;

SINGER, RD .

CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188

[22] TMP-zincate as highly chemoselective base for directed ortho metalation [J].

Kondo, Y ;

Shilai, M ;

Uchiyama, M ;

Sakamoto, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) :3539-3540

[23] Palladium-catalyzed arylation of trimethylsilyl enolates of esters and imides.: High functional group tolerance and stereoselective synthesis of α-aryl carboxylic acid derivatives [J].

Liu, XX ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5182-5191

[24] Modern ate chemistry: Applications of synergic mixed alkali-metal-magnesium or -zinc reagents in synthesis and structure building [J].

Mulvey, RE .

ORGANOMETALLICS, 2006, 25 (05) :1060-1075

[25] EFFECT OF SOLVENTS ON REACTIONS OF ORGANOMETALLIC COMPOUNDS .V. EFFECT OF SOLVATION ON ZINC ALKYL CAPACITY FOR METALATION REACTIONS [J].

OKHLOBYSTIN, OY ;

ZAKHARKIN, LI .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1965, 3 (03) :257-+

[26]

POZHARSKI AF, 1997, HETEROCYCLES LIFE SO

[27] First structural characterization of a zinc-bis(dialkylamide) compound:: Zn{N[C(CH3)2(CH2)3C(CH3)2]} [J].

Rees, WS ;

Just, O ;

Schumann, H ;

Weimann, R .

POLYHEDRON, 1998, 17 (5-6) :1001-1004

[28] STRUCTURE AND REACTIVITY OF LITHIUM ENOLATES - FROM PINACOLONE TO SELECTIVE C-ALKYLATIONS OF PEPTIDES - DIFFICULTIES AND OPPORTUNITIES AFFORDED BY COMPLEX STRUCTURES [J].

SEEBACH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (12) :1624-1654

[29] α-zincated phosphorus ylides [J].

Steiner, M ;

Grützmacher, H ;

Prtizkow, H ;

Zsolnai, L .

CHEMICAL COMMUNICATIONS, 1998, (02) :285-286

[30] A direct catalytic enantioselective aldol reaction via a novel catalyst design [J].

Trost, BM ;

Ito, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12003-12004

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