Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans

Yahui Wang; Adam Noble; Christopher Sandford; Varinder K. Aggarwal

doi:10.1002/anie.201611058

Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans

Yahui Wang, Adam Noble, Christopher Sandford, Varinder K. Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

51 Citations (Scopus)

358 Downloads (Pure)

Abstract

In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.

Original language	English
Pages (from-to)	1810-1814
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	7
Early online date	30 Jan 2017
DOIs	https://doi.org/10.1002/anie.201611058
Publication status	Published - 6 Feb 2017

Keywords

boronic esters
cross-coupling
furans
stereospecificity
trifluoromethylation

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EMTECS: MSC Fellowship: Yahui Wang
Aggarwal, V. K. (Principal Investigator)
1/03/15 → 28/02/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research

Dr Adam Noble
- a.noblebristol.acuk
- School of Chemistry - Lecturer
Person: Academic

Cite this

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title = "Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans",

abstract = "In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.",

keywords = "boronic esters, cross-coupling, furans, stereospecificity, trifluoromethylation",

author = "Yahui Wang and Adam Noble and Christopher Sandford and Aggarwal, {Varinder K.}",

year = "2017",

month = feb,

day = "6",

doi = "10.1002/anie.201611058",

language = "English",

volume = "56",

pages = "1810--1814",

journal = "Angewandte Chemie - International Edition",

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publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans

AU - Wang, Yahui

AU - Noble, Adam

AU - Sandford, Christopher

AU - Aggarwal, Varinder K.

PY - 2017/2/6

Y1 - 2017/2/6

N2 - In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.

AB - In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.

KW - boronic esters

KW - cross-coupling

KW - furans

KW - stereospecificity

KW - trifluoromethylation

U2 - 10.1002/anie.201611058

DO - 10.1002/anie.201611058

M3 - Article (Academic Journal)

C2 - 28097819

AN - SCOPUS:85009826770

SN - 1433-7851

VL - 56

SP - 1810

EP - 1814

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans

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Keywords

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Projects

EMTECS: MSC Fellowship: Yahui Wang

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Profiles

Dr Adam Noble

Cite this