Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls

被引：151

作者：

Liang, Zuijun ^{[1
]}

Zhao, Jinlong ^{[1
]}

Zhang, Yuhong ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 01期

关键词：

DIRECT C-2 ARYLATION; H BOND ARYLATION; DIRECT FUNCTIONALIZATION; ROOM-TEMPERATURE; ARYL BROMIDES; C-O; ACTIVATION; ALDEHYDES; ACID; ALKENYLATION;

D O I：

10.1021/jo902265s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mild conditions have been developed to achieve Pd-catalyzed homocoupling of indoles with excellent regioselectivity in the presence of Cu(OAc)(2)center dot H2O in DMSO at room temperature in high efficiency. This method provides a simple route to 2,3-biindolyls from the electron-rich to moderately electron-poor indoles. The reaction tolerates the bromide substitLient on indoles. In addition, a one-pot approach to C3-position acetoxylated biindolyls is realized via palladium catalysis by the use of AgOAc under oxygen atmosphere as oxidants.

引用

页码：170 / 177

页数：8

共 50 条

[41] Palladium-Catalyzed Acylation Reactions: A One-Pot Diversified Synthesis of Phthalazines, Phthalazinones and Benzoxazinones
Suchand, Basuli
Satyanarayana, Gedu
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (19) : 2233 - 2246
[42] One-pot palladium-catalyzed cross-coupling reaction of aryl iodides with stannylarsanes and stannylstibanes
Bonaterra, M
Martín, SE
Rossi, RA
ORGANIC LETTERS, 2003, 5 (15) : 2731 - 2734
[43] Palladium-catalyzed γ-arylation of β,γ-unsaturated ketones:: Application to a one-pot synthesis of tricyclic indolines
Hyde, Alan M.
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (01) : 177 - 180
[44] Palladium-Catalyzed N-Monoarylation of Amidines and a One-Pot Synthesis of Quinazoline Derivatives
McGowan, Meredeth A.
McAvoy, Camille Z.
Buchwald, Stephen L.
ORGANIC LETTERS, 2012, 14 (14) : 3800 - 3803
[45] One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
Jong, Howard
Eey, Stanley T. -C.
Lim, Yee Hwee
Pandey, Sangeeta
Iqbal, Nurul Azmah Bte
Yong, Fui Fong
Robins, Edward G.
Johannes, Charles W.
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (04) : 616 - 622
[46] Development of a one-pot palladium-catalyzed hydrostannylation/stille coupling protocol with catalytic amounts of tin
Maleczka, RE
Terstiege, I
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26): : 9622 - 9623
[47] Synthesis of unsymmetrical triarylamines for photonic applications via one-pot palladium-catalyzed aminations
Thayumanavan, S
Barlow, S
Marder, SR
CHEMISTRY OF MATERIALS, 1997, 9 (12) : 3231 - 3235
[48] Palladium-Catalyzed Oxidative Amination of α-Olefins with Indoles
Bhatt, Shreeja
Wang, Ya-Nong
Pham, Hoang T. P.
Hull, Kami L.
ORGANIC LETTERS, 2022, 24 (31) : 5746 - 5750
[49] TBAF catalyzed one-pot synthesis of allenyl-indoles
De Nisi, A.
Sierra, S.
Ferrara, M.
Monari, M.
Bandini, M.
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (09): : 1849 - 1853
[50] Palladium-catalyzed synthesis of fused indoles
Söderberg, BC
Rector, SR
O'Neil, SN
TETRAHEDRON LETTERS, 1999, 40 (19) : 3657 - 3660

← 1 2 3 4 5 →