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Synthesis 2010(5): 882-891
DOI: 10.1055/s-0029-1217134
DOI: 10.1055/s-0029-1217134
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
Large-Scale Preparation of Polyfunctional Benzylic Zinc Reagents by Direct Insertion of Zinc Dust into Benzylic Chlorides in the Presence of Lithium Chloride
Weitere Informationen
Received
21 September 2009
Publikationsdatum:
20. November 2009 (online)
Publikationsverlauf
Publikationsdatum:
20. November 2009 (online)
Abstract
Highly functionalized benzylic zinc chlorides are prepared by the direct insertion of commercially available zinc dust into the corresponding benzylic chlorides in the presence of stoichiometric amount of lithium chloride. These polyfunctional zinc organometallics react with various electrophiles leading to a broad range of functionalized products.
Key words
insertion - zinc organometallics - zinc - benzylic zinc chlorides - lithium chloride
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1a
Knochel P.Singer RD. Chem. Rev. 1993, 93: 2117 -
1b
Knochel P.Millot N.Rodriguez A.Tucker CE. Org. React. 2001, 58: 417 -
1c
Knochel P. In Handbook of Functionalized Organometallics Wiley-VCH; Weinheim: 2005. - 2
Krasovskiy A.Malakhov V.Gavryushin A.Knochel P. Angew. Chem. Int. Ed. 2006, 45: 6040 - 3
Metzger A.Schade MA.Knochel P. Org. Lett. 2008, 10: 1107 - 4
Stoll AH.Krasovskiy A.Knochel P. Angew. Chem. Int. Ed. 2007, 46: 606 - 5 Yield indicated by iodometric titration;
see also:
Krasovskiy A.Knochel P. Synthesis 2006, 890 - 6
Knochel P.Yeh MCP.Berk SC.Talbert J. J. Org. Chem. 1988, 53: 2390 - 7
Villieras J.Rambaud M. Synthesis 1982, 924 - 8 According to:
Berk SC.Yeh MCP.Jeong N.Knochel P. Organometallics 1990, 9: 3053