Bifunctional Skipped Dienes through Cu/Pd-Catalyzed Allylboration of Alkynes with B2pin2 and Vinyl Epoxides

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2022_orglet_vazquez_bifunctional.pdf (1.68 MB)
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URI: http://hdl.handle.net/10347/29690
ISSN: 1523-7060
E-ISSN: 1523-7052
DOI: 10.1021/acs.orglett.2c03390

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2022

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ACS Publications
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Abstract

A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described. This transformation allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These two functionalities provide these products with highly versatile reactivity, as shown by their stereocontrolled conversion into cyclic boron compounds and polyenes.

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Chemical reactions| Ethers| Hydrocarbons| Inorganic carbon compounds| Vinyl

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https://doi.org/10.1021/acs.orglett.2c03390

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Financial support from AEI (PID2020-118237RB-I00), the European Research Council (863914), the Xunta de Galicia (Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03), and the European Regional Development Fund (ERDF) is gratefully acknowledged. N.V.-G. thanks AEI for an FPI Predoctoral Fellowship

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© 2022 The Authors. Published by American Chemical Society. This work is under a CC Attribution 4.0 International (CC BY 4.0)
Atribución 4.0 Internacional

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Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica