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Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines

Harathi D. Srinivas, Qi Zhou and Mary P. Watson*

*Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email: mpwatsonudel.edu

H. D. Srinivas, Q. Zhou, M. P. Watson, Org. Lett., 2014, 16, 3596-3599.

DOI: 10.1021/ol5016724 (free Supporting Information)


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Abstract

The success of a regioselective and enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines relies on the use of BnPPh2 as a supporting ligand and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields.


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Key Words

allylation


ID: J54-Y2014