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Nickel-Catalyzed Carbon−Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations

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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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja311669pDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja311669pPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3547142/PubMed CentralArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
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.
Funders:
Funding AgencyGrant Number
NIHR01-GM62871
Merck Research LaboratoriesUNSPECIFIED
PubMed Central ID:PMC3547142
Record Number:CaltechAUTHORS:20130221-102120190
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20130221-102120190
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.
ID Code:37050
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:21 Feb 2013 23:55
Last Modified:12 Dec 2016 20:54

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