Synthesis of diverse allylsilanes employing brønsted acid catalyzed reductive functionalization

Elisabeth L. R. Leonard; Geoffrey R. Akien; Thomas K. Britten; Nahin Kazi; Dean D. Roberts; Mark G. McLaughlin

doi:10.1002/adsc.202300917

Synthesis of diverse allylsilanes employing brønsted acid catalyzed reductive functionalization

Elisabeth L. R. Leonard, Geoffrey R. Akien, Thomas K. Britten, Nahin Kazi, Dean D. Roberts, Mark G. McLaughlin^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

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Abstract

We present a rapid (0.25–1 h), method to produce functionalised allylsilanes from readily available vinylsilanes. Employing a Brønsted acid catalysed dehydration as the key step, allylsilanes are produced in good yields (22–98%) and, in most cases, as a single geometric isomer. Furthermore, a possible allylation-Cope pathway was discovered for certain substrates and attempts to optimise this are described.

Original language	English
Pages (from-to)	3872-3875
Number of pages	4
Journal	Advanced Synthesis & Catalysis
Volume	365
Issue number	22
Early online date	06 Nov 2023
DOIs	https://doi.org/10.1002/adsc.202300917
Publication status	Published - 21 Nov 2023

Keywords

Dehydration
Homogeneous catalysis
Allylation
Bronsted Acid Catalysis
Organosilanes

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10.1002/adsc.202300917Licence: CC BY

Synthesis of diverse allylsilanes employing brønsted acid catalyzed reductive functionalization
Copyright 2023 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, 4.02 MBLicence: CC BY

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abstract = "We present a rapid (0.25–1 h), method to produce functionalised allylsilanes from readily available vinylsilanes. Employing a Br{\o}nsted acid catalysed dehydration as the key step, allylsilanes are produced in good yields (22–98%) and, in most cases, as a single geometric isomer. Furthermore, a possible allylation-Cope pathway was discovered for certain substrates and attempts to optimise this are described.",

keywords = "Dehydration, Homogeneous catalysis, Allylation, Bronsted Acid Catalysis, Organosilanes",

author = "Leonard, {Elisabeth L. R.} and Akien, {Geoffrey R.} and Britten, {Thomas K.} and Nahin Kazi and Roberts, {Dean D.} and McLaughlin, {Mark G.}",

year = "2023",

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doi = "10.1002/adsc.202300917",

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T1 - Synthesis of diverse allylsilanes employing brønsted acid catalyzed reductive functionalization

AU - Leonard, Elisabeth L. R.

AU - Akien, Geoffrey R.

AU - Britten, Thomas K.

AU - Kazi, Nahin

AU - Roberts, Dean D.

AU - McLaughlin, Mark G.

PY - 2023/11/21

Y1 - 2023/11/21

N2 - We present a rapid (0.25–1 h), method to produce functionalised allylsilanes from readily available vinylsilanes. Employing a Brønsted acid catalysed dehydration as the key step, allylsilanes are produced in good yields (22–98%) and, in most cases, as a single geometric isomer. Furthermore, a possible allylation-Cope pathway was discovered for certain substrates and attempts to optimise this are described.

AB - We present a rapid (0.25–1 h), method to produce functionalised allylsilanes from readily available vinylsilanes. Employing a Brønsted acid catalysed dehydration as the key step, allylsilanes are produced in good yields (22–98%) and, in most cases, as a single geometric isomer. Furthermore, a possible allylation-Cope pathway was discovered for certain substrates and attempts to optimise this are described.

KW - Dehydration

KW - Homogeneous catalysis

KW - Allylation

KW - Bronsted Acid Catalysis

KW - Organosilanes

U2 - 10.1002/adsc.202300917

DO - 10.1002/adsc.202300917

M3 - Article

SN - 1615-4169

VL - 365

SP - 3872

EP - 3875

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 22

ER -

Synthesis of diverse allylsilanes employing brønsted acid catalyzed reductive functionalization

Abstract

Keywords

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