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Ir-Catalyzed Selective Hydroboration of 2-Substituted 1,3-Dienes: A General Method to Access Homoallylic Boronates

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Published in ACS Catalysis. 2018, vol. 8, no. 10, p. 9382-9387
Abstract 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 the 2-position, it provides access to a variety of homoallylic boronates featuring a 1,1-disubstituted olefin in high yield and 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.
Keywords Conjugated 1,3-dienesHomoallylic boronatesHydroborationIridium catalysisSelective catalysis
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Other version: http://pubs.acs.org/doi/10.1021/acscatal.8b02334
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Research group Groupe Mazet
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FIORITO, Daniele, MAZET, Clement. Ir-Catalyzed Selective Hydroboration of 2-Substituted 1,3-Dienes: A General Method to Access Homoallylic Boronates. In: ACS Catalysis, 2018, vol. 8, n° 10, p. 9382-9387. https://archive-ouverte.unige.ch/unige:107880

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Deposited on : 2018-09-17

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