Zultanski, Susan L. and Fu, Gregory C. (2013) Nickel-Catalyzed Carbon−Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations. Journal of the American Chemical Society, 135 (2). pp. 624-627. ISSN 0002-7863. PMCID PMC3547142. http://resolver.caltech.edu/CaltechAUTHORS:20130221-102120190
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The first Suzuki cross-couplings of unactivated tertiary alkyl electrophiles are described. The method employs a readily accessible catalyst (NiBr_2·diglyme/4,4′-di-tert-butyl-2,2′-bipyridine, both commercially available) and represents the initial example of the use of a group 10 catalyst to cross-couple unactivated tertiary electrophiles to form C–C bonds. This approach to the synthesis of all-carbon quaternary carbon centers does not suffer from isomerization of the alkyl group, in contrast with the umpolung strategy for this bond construction (cross-coupling of a tertiary alkylmetal with an aryl electrophile). Preliminary mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.
|Additional Information:||© 2013 American Chemical Society. Received: November 29, 2012; published: January 2, 2013. Support was provided by the National Institutes of Health (National Institute of General Medical Sciences, R01-GM62871) and Merck Research Laboratories (summer fellowship for S.L.Z.). We thank Dr. Alexander S. Dudnik for preliminary observations.|
|PubMed Central ID:||PMC3547142|
|Official Citation:||Nickel-Catalyzed Carbon–Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations Susan L. Zultanski and Gregory C. Fu Journal of the American Chemical Society 2013 135 (2), 624-627|
|Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Jason Perez|
|Deposited On:||21 Feb 2013 23:55|
|Last Modified:||12 Dec 2016 20:54|
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