Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis 英文参考文献.docVIP

Molecules 2010, 15, 8006-8038; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Recent Advance in Heterocyclic Organozinc and Organomanganese Compounds; Direct Synthetic Routes and Application in Organic Synthesis Seung-Hoi Kim 1 and Reuben D. Rieke 2,* 1 Department of Chemistry, Dankook University; 29 Anseo Cheonan Chungnam, 330-714, Korea; E-Mail: kimsemail@dankook.ac.kr (S-H.K.); Tel.: 82-41-550-1816 2 Rieke Metals, Inc.; 1001 Kingbird Rd. Lincoln, NE 68512, USA * Author to whom correspondence should be addressed; E-Mail: sales@; Tel.: +1-402-434-2775; Fax: +1-402-434-2777. Received: 17 September 2010; in revised form: 1 November 2010 / Accepted: 4 November 2010 / Published: 8 November 2010 Abstract: A practical synthetic route for the preparation of 2-pyridyl and 3-pyridyl derivatives has been accomplished by utilizing a simple coupling reaction of stable 2- pyridylzinc bromides and 3-pyridylzinc bromides. The organozincs used in this study were easily prepared via the direct insertion of active zinc into the corresponding bromopyridines. The subsequent coupling reactions with a variety of different electrophiles have afforded the corresponding coupling products. Using highly active manganese, a variety of Grignard-type organomanganese reagents have been obtained. The subsequent coupling reactions of the resulting organomanganese reagents with several electrophiles have also been accomplished under mild conditions. Keywords: highly active metals; organozinc; organomanganese; heterocyclic compounds 1. Introduction In 1972, Rieke and co-workers reported a general approach for preparing highly active metal powders (called Rieke metals) by reducing metal salts in ethereal or hydrocarbon solvents using alkali metals as reducing reagents [1]. A second general approach for the preparation of Rieke metals involves using an