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Author(s): Anctil EJG; Snieckus V
Title: The directed ortho metalation - cross coupling symbiosis. Regioselective methodologies for biaryls and heterobiaryls. Deployment in aromatic and heteroaromatic natural product synthesis
Source: JOURNAL OF ORGANOMETALLIC CHEMISTRY 653 (1-2): 150-160
Date: 2002 JUL 1
Document Type: Journal : Proceedings Paper
DOI:
Language: English
Comment:
Address: Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada.
Reprint: Snieckus, V, Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada.
E-mail:
Author Keywords: directed ortho metalation; cross coupling; biaryls; heteroaromatics;
natural products; synthesis
KeyWords Plus: PALLADIUM-CATALYZED AMINATION; GENERAL REGIOSPECIFIC ROUTE; ARYLBORONIC
ACIDS; ARYL HALIDES; ORGANIC HALIDES; BOND FORMATION; CONNECTIONS;
STRATEGIES; KINOBSCURINONE; PREKINAMYCIN
Abstract: In this mini-review, synthetic methods for biaryls and heterobiaryls interconnecting the directed ortho metalation (DoM) reaction with Corriu-Kumada, Negishi, Suzuki-Miyaura and, less, Stille cross coupling reactions are presented from perspectives of development of new reaction parameters (Suzuki-Miyaura: Schemes 4-7), new cross coupling partners (Corriu-Kumada: Schemes 9 and 11), and comprehensive evaluation (Schemes 12 and 13). Recent work on the application of these protocols to indole derivatives (Schemes 16-18), dibenzopyranones (Scheme 19), aza-and isoazacoumestans (Scheme 20), and kinamycin antibiotics (Scheme 21) is described. (C) 2002 Elsevier Science B.V. All rights reserved.
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