3-Zinciobenzofuran and 3-zincioindole: Versatile tools for the construction of conjugated structures containing multiple benzoheterole units

被引：133

作者：

Nakamura, M ^{[1
]}

Ilies, L

Otsubo, S

Nakamura, E

机构：

[1] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Univ Tokyo, ERATO, Nakamura Funct Carbon Cluster Project, Japan Sci & Technol Agcy,Bunkyo Ku, Tokyo 1130033, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 06期

关键词：

benzoheterole; conjugation; cyclization; heterocycles; palladium; zinc;

D O I：

10.1002/anie.200502920

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Closing the ring: Thermally stable but reactive 3-zinciobenzofurans and indoles were synthesized by metalative cyclization of 2-ynyl phenols or anilines. Furthermore, a variety of extended π-conjugated molecules were obtained by Pd-catalyzed cross-coupling reactions of these heterocycles with mono- or polyhalo-substituted arenes and alkenes (R2Haln; see scheme; Bn = benzyl). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：944 / 947

页数：4

共 33 条

[21] MERCURY IN ORGANIC-CHEMISTRY .26. SYNTHESIS OF HETEROCYCLES VIA INTRAMOLECULAR SOLVOMERCURATION OF ARYL ACETYLENES [J].

LAROCK, RC ;

HARRISON, LW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4218-4227

[22] THEORETICAL-STUDIES OF HETEROATOM-DIRECTED CARBOMETALATION - ADDITION OF MECU, ME2CU-, AND MELI TO SUBSTITUTED ACETYLENES [J].

NAKAMURA, E ;

MIYACHI, Y ;

KOGA, N ;

MOROKUMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6686-6692

[23] Stereoselective synthesis of tetra-substituted olefins via addition of zinc enolates to unactivated alkynes [J].

Nakamura, M ;

Fujimoto, T ;

Endo, K ;

Nakamura, E .

ORGANIC LETTERS, 2004, 6 (26) :4837-4840

[24] α-alkylation of ketones by addition of zinc enamides to unactivated olefins [J].

Nakamura, M ;

Hatakeyama, T ;

Nakamura, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11820-11825

[25] Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: A one-pot synthesis of methylenetetrahydrofurans [J].

Nakamura, M ;

Liang, CG ;

Nakamura, E .

ORGANIC LETTERS, 2004, 6 (12) :2015-2017

[26] Enantioselective synthesis of α-substituted ketones by asymmetric addition of chiral zinc enamides to 1-alkenes [J].

Nakamura, M ;

Hatakeyama, T ;

Hara, K ;

Nakamura, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6362-6363

[27] Indium-catalyzed addition of active methylene compounds to 1-alkynes [J].

Nakamura, M ;

Endo, K ;

Nakamura, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (43) :13002-13003

[28] Reaction pathways of the Simmons-Smith reaction [J].

Nakamura, M ;

Hirai, A ;

Nakamura, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2341-2350

[29] The double N-arylation of primary amines:: Toward multisubstituted carbazoles with unique optical properties [J].

Nozaki, K ;

Takahashi, K ;

Nakano, K ;

Hiyama, T ;

Tang, HZ ;

Fujiki, M ;

Yamaguchi, S ;

Tamao, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2051-2053

[30]

Nozaki K, 2003, ANGEW CHEM, V115, P2097, DOI DOI 10.1002/ANGE.200250648

← 1 2 3 4 →