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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 5
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Original Articles

Convenient Method for the Preparation of the 2-Methyl Thiophen-3-yl Magnesium Bromide Lithium Chloride Complex and Its Application to the Synthesis of 3-Substituted 2-Methylthiophenes

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Pages 681-688 | Received 24 May 2011, Published online: 13 Nov 2012

REFERENCES

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  • (a) Rieke , R. D. ; Kim , S.-H. ; Wu , X. Direct preparation of 3-thienyl organometallic reagents: 3-Thienylzinc and 3-thienylmagnesium iodides and 3-thienylmagnesium bromides and their coupling reactions . J. Org. Chem. 1997 , 62 , 6921 ; (b) Alcaraz , M.-L. ; Atkinson , S. ; Cornwall , P. ; Foster , A. C. ; Gill , D. M. ; Humphries , L. A. ; Keegan , P. S. ; Kemp , R. ; Merifield , E. ; Nixon , R. A. ; Noble , A. J. ; O'Beirne , D. ; Patel , Z. M. ; Perkins , J. ; Rowan , P. ; Sadler , P. ; Singleton , J. T. ; Tornos , J. ; Watts , A. J. ; Woodland , I. A. Efficient synthesis of AZD4407 via thioester formation by nucleophilic attack of organometallic species on sulfur . Org. Process Res. Dev. 2005 , 9 , 555 .
  • For reviews for activation of magnesium metal, see (a) Tilstam , U. ; Weinmann , H. Activation of Mg metal for safe formation of Grignard reagents on plant scale. Org. Process Res. Dev. 2002, 6, 906; (b) Furstner , A. Chemistry of and with highly reactive metals. Angew. Chem., Int. Ed. Engl. 1993, 32, 164; (c) Lai , Y.-H. Grignard reagents from chemically activated magnesium. Synthesis 1981, 585; (d) For a recent review, see Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl. Piller , F. M. ; Metzger , A. ; Schade , M. A. ; Haag , B. A. ; Gavryushin , A. ; Knochel , P. Chem. Eur. J. 2009, 15, 7192.
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