An operationally simple, regioselective, platinum-catalyzed hydroboration of unactivated alkynes

K. Lawrence E.  Hale; Dean D. Roberts; Mark G. McLaughlin

doi:10.1002/ejoc.202401355

An operationally simple, regioselective, platinum-catalyzed hydroboration of unactivated alkynes

K. Lawrence E. Hale, Dean D. Roberts, Mark G. McLaughlin^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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Abstract

Herein is reported a new PtCl₂/XPhos/Et₃SiH-catalyzed hydroboration method for unactivated terminal alkynes. Significantly, the reaction proceeds in hindered alkyne systems, and works well on acetylenes that contain multiple heteroatom-groups to provide the desired (E)-1,2-vinyl boronates in reasonable to high yields with excellent levels of stereo- and regio-control.

Original language	English
Article number	e202401355
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	28
Issue number	11
Early online date	06 Feb 2025
DOIs	https://doi.org/10.1002/ejoc.202401355
Publication status	Published - 17 Mar 2025

Keywords

alkyne
hydroboration
platinum
vinyl boronate

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10.1002/ejoc.202401355Licence: CC BY

An operationally simple, regioselective, platinum-catalyzed hydroboration of unactivated alkynes
Copyright 2025 The Authors. This is an open access article published under a Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Final published version, 4.01 MBLicence: CC BY

Cite this

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AU - Hale, K. Lawrence E.

AU - Roberts, Dean D.

AU - McLaughlin, Mark G.

PY - 2025/3/17

Y1 - 2025/3/17

N2 - Herein is reported a new PtCl2/XPhos/Et3SiH-catalyzed hydroboration method for unactivated terminal alkynes. Significantly, the reaction proceeds in hindered alkyne systems, and works well on acetylenes that contain multiple heteroatom-groups to provide the desired (E)-1,2-vinyl boronates in reasonable to high yields with excellent levels of stereo- and regio-control.

AB - Herein is reported a new PtCl2/XPhos/Et3SiH-catalyzed hydroboration method for unactivated terminal alkynes. Significantly, the reaction proceeds in hindered alkyne systems, and works well on acetylenes that contain multiple heteroatom-groups to provide the desired (E)-1,2-vinyl boronates in reasonable to high yields with excellent levels of stereo- and regio-control.

KW - alkyne

KW - hydroboration

KW - platinum

KW - vinyl boronate

U2 - 10.1002/ejoc.202401355

DO - 10.1002/ejoc.202401355

M3 - Article

SN - 1099-0690

VL - 28

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 11

M1 - e202401355

ER -

An operationally simple, regioselective, platinum-catalyzed hydroboration of unactivated alkynes

Abstract

Keywords

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