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Publication 60  

  1. Ir-Catalyzed Selective Hydroboration of 2-Substituted 1,3-Dienes: A General Method to Access Homoallylic Boronates
    Daniele Fiorito, Clément Mazet*
    ACS Catal. 2018, 8, 9382-9387

An operationally simple protocol for the 4,3-selective hydroboration of 2-substituted 1,3-dienes using an iridium catalyst is described. Independently of the nature (alkyl, aryl, heteroaryl) and the size of the substituent in 2-position, it provides access to a variety of homoallylic boronates featuring a 1,1-disubstituted olefin in high yield, chemo- and regioselectivity. An array of potentially sensitive functional groups is well-tolerated and the method can be extend to 1,2-disubstituted 1,3-dienes. Derivatization of the homoallylic boronates is also demonstrated using contemporary catalytic and enantioselective processes.

open archive unige:107880

Editor’s version DOI: 10.1021/acscatal.8b02334 

AAM DOI: 10.26037/yareta:c4y44m4cjzhgbnhlx2kycfyetu 

Dataset DOI: 10.26037/yareta:dawn4odedfa4zjtwgmeh2d2lbq