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NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

Won Jun Jang, Jung Tae Han, Jaesook Yun*

*Department of Chemistry and Institute of Basic Science, Sungkyunkwan University, Suwon 16419, Korea, Email: jaesookskku.edu

W. J. Jang, J. T. Han, J. Yun, Synthesis, 2017, 49, 4753-4758.

DOI: 10.1055/s-0036-1588811 (free Supporting Information)


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Abstract

In the presence of IMes-Cu catalyst, a tandem hydrocupration/allylation of alkenyl boronates with allyl phosphate efficiently proceeds in the presence of a hydrosilane via in situ generated Β-α-copper intermediates. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

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Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation

J. T. Han, W. J. Jang, N. Kim, J. Yun, J. Am. Chem. Soc., 2016, 138, 15146-15149.


Key Words

allylic substitution, copper, homoallylic boronates, hydrocupration, N-heterocyclic carbenes, tandem reaction, PMHS


ID: J66-Y2017