Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

Susana Estopiñá-Durán; Euan B. Mclean; Liam Donnelly; Bryony M. Hockin; James E. Taylor

doi:10.1021/acs.orglett.0c02736

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

Susana Estopiñá-Durán, Euan B. Mclean, Liam Donnelly, Bryony M. Hockin, James E. Taylor^*

^*Corresponding author for this work

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

27 Citations (Scopus)

2 Downloads (Pure)

Abstract

The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

Original language	English
Pages (from-to)	7547-7551
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.0c02736
Publication status	Published - 2 Oct 2020

Keywords

Alcohols
Allylation
Electrophiles
Reaction Roducts
Substitution Reactions

Access to Document

10.1021/acs.orglett.0c02736Licence: CC BY

Download pdf
Copyright © 2020 American Chemical Society. This publication is licensed under CC-BY 4.0 .
Final published version, 1.17 MBLicence: CC BY

Cite this

@article{de1819f2c9004a16a4c416c540e753e2,

title = "Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols",

abstract = "The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).",

keywords = "Alcohols, Allylation, Electrophiles, Reaction Roducts, Substitution Reactions",

author = "Susana Estopi{\~n}{\'a}-Dur{\'a}n and Mclean, {Euan B.} and Liam Donnelly and Hockin, {Bryony M.} and Taylor, {James E.}",

year = "2020",

month = oct,

day = "2",

doi = "10.1021/acs.orglett.0c02736",

language = "English",

volume = "22",

pages = "7547--7551",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

AU - Estopiñá-Durán, Susana

AU - Mclean, Euan B.

AU - Donnelly, Liam

AU - Hockin, Bryony M.

AU - Taylor, James E.

PY - 2020/10/2

Y1 - 2020/10/2

N2 - The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

AB - The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

KW - Alcohols

KW - Allylation

KW - Electrophiles

KW - Reaction Roducts

KW - Substitution Reactions

U2 - 10.1021/acs.orglett.0c02736

DO - 10.1021/acs.orglett.0c02736

M3 - Article

SN - 1523-7060

VL - 22

SP - 7547

EP - 7551

JO - Organic letters

JF - Organic letters

IS - 19

ER -

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

Abstract

Keywords

Access to Document

Fingerprint

Cite this