title: Synthesis of Branched Alkylboronates by Copper-Catalyzed Allylic Substitution Reactions of Allylic Chlorides with 1,1-Diborylalkanes.
abstract: Reported herein is a copper-catalyzed S(N)2'-selective allylic substitution reaction using readily accessible allylic chlorides and 1,1-diborylalkanes, a reaction which proceeds with chemoselective C-B bond activation of the 1,1-diborylalkanes. In the presence of a catalytic amount of [Cu(IMes)Cl] [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene] and LiOtBu as a base, a range of primary and secondary allylic chlorides undergo the S(N)2'-selective allylic substitution reaction to produce branched alkylboronates. The synthetic utilities of the obtained alkylboronates are also presented.
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Republic of Korea.
authors.forename: Junghoon
authors.initials: J
authors.lastname: Kim
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Republic of Korea.
authors.forename: Sangwoo
authors.initials: S
authors.lastname: Park
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Republic of Korea.
authors.forename: Jinyoung
authors.initials: J
authors.lastname: Park
authors.affiliation: Department of Chemistry and Division of Advanced Nuclear Engineering, Pohang University of Science and Technology (POSTECH), Pohang, 790-784, Republic of Korea. seunghwan@postech.ac.kr.
authors.forename: Seung Hwan
authors.initials: SH
authors.lastname: Cho
keywords: N-heterocyclic carbenes; allylic compounds; boron; copper; regioselectivity