Regio- and Chemoselective Zincation of Sensitive and Moderately Activated Aromatics and Heteroaromatics Using TMPZnCl•LiCl

被引：64

作者：

Bresser, Tomke ^{[1
]}

Mosrin, Marc ^{[1
]}

Monzon, Gabriel ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 14期

基金：

欧洲研究理事会;

关键词：

MULTIPLE FUNCTIONALIZATION; PYRIMIDINE-DERIVATIVES; DIRECTED ZINCATION; TMP-ZINCATE; METALATION; MAGNESIATION; ARENES; ROUTE; BASE; GENERATION;

D O I：

10.1021/jo100884u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broad range of functionalized aryl- and heteroarylzinc reagents were prepared via directed zincation of sensitive and moderately activated aromatics and heteroaromatics using TMPZnCl center dot LiCl under various reaction conditions. Diverse sensitive functional groups such as a nitro group, an aldehyde, an ester, and a nitrile are readily tolerated and are compatible with high metalation temperatures. Furthermore, the resulting zinc organometallics display an excellent reactivity toward various classes of electrophiles providing functionalized aromatics and heteroaromatics in high yields.

引用

收藏

页码：4686 / 4695

页数：10

相关论文

共 35 条

[21] Deprotonative metalation using ate compounds: Synergy, synthesis, and structure building [J].

Mulvey, Robert E. ;

Mongin, Florence ;

Uchiyama, Masanobu ;

Kondo, Yoshinori .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3802-3824

[22] An aluminum ate base: Its design, structure, function, and reaction mechanism [J].

Naka, Hiroshi ;

Uchiyama, Masanobu ;

Matsumoto, Yotaro ;

Wheatley, Andrew E. H. ;

McPartlin, Mary ;

Morey, James V. ;

Kondo, Yoshinori .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) :1921-1930

[23] SELECTIVE CARBON-CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .36. PALLADIUM-CATALYZED ACYLATION OF ORGANOZINCS AND OTHER ORGANOMETALLICS AS A CONVENIENT ROUTE TO KETONES [J].

NEGISHI, E ;

BAGHERI, V ;

CHATTERJEE, S ;

LUO, FT ;

MILLER, JA ;

STOLL, AT .

TETRAHEDRON LETTERS, 1983, 24 (47) :5181-5184

[24]

NEGISHI E, 1980, J AM CHEM SOC, V102, P3298, DOI 10.1021/ja00529a091

[25] PALLADIUM-CATALYZED OR NICKEL-CATALYZED CROSS COUPLING - A NEW SELECTIVE METHOD FOR CARBON CARBON BOND FORMATION [J].

NEGISHI, EI .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (11) :340-348

[26] A general method for meta and para functionalization of arenes using TMP2Mg•2LiCl [J].

Rohbogner, Christoph J. ;

Clososki, Giuliano C. ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1503-1507

[27] Phosphorodiamidate-Directed Metalation of N-Heterocycles using Mg- and Zn-TMP Bases [J].

Rohbogner, Christoph J. ;

Wirth, Stefan ;

Knochel, Paul .

ORGANIC LETTERS, 2010, 12 (09) :1984-1987

[28] DIRECTED ORTHO METALATION - TERTIARY AMIDE AND O-CARBAMATE DIRECTORS IN SYNTHETIC STRATEGIES FOR POLYSUBSTITUTED AROMATICS [J].

SNIECKUS, V .

CHEMICAL REVIEWS, 1990, 90 (06) :879-933

[29] CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES [J].

SONOGASHIRA, K ;

TOHDA, Y ;

HAGIHARA, N .

TETRAHEDRON LETTERS, 1975, (50) :4467-4470

[30]

Sonogashira K., 1991, COMPREHENSIVE ORGANI, V3

← 1 2 3 4 →