The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes

Andrew J. Smith; Darren L. Poole; John A. Murphy

doi:10.1007/s11426-019-9611-x

The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes

Andrew J. Smith, Darren L. Poole, John A. Murphy

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

22 Citations (Scopus)

26 Downloads (Pure)

Abstract

Coupling reactions between haloarenes and arenes (including heteroarenes) that are conducted without added transition metals but in the presence of KOtBu or NaOtBu, have been a topic of great interest since their discovery in 2008. Diverse organic structures act as additives that assist these reactions. These additives are converted into organic electron donors by the butoxide base and this leads to initiation of the coupling reactions, which proceed by radical chain mechanisms. This review provides an overview of the initiation stages of these reactions.

Original language	English
Pages (from-to)	1425-1438
Number of pages	14
Journal	Science China Chemistry
Volume	62
Issue number	11
Early online date	17 Oct 2019
DOIs	https://doi.org/10.1007/s11426-019-9611-x
Publication status	Published - 30 Nov 2019

Keywords

organic electron donor
benzyne
BHAS coupling
electron transfer
potassium tert-butoxide

Access to Document

10.1007/s11426-019-9611-x

Smith-etal-SCC-2019-The-role-of-organic-electron-donors-in-the-initiation-of-BHAS-base-induced-couplingAccepted author manuscript, 1.25 MB

Industrial Case Account 2015 / S151217-105
Murphy, J. (Principal Investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/10/15 → 30/09/20
Project: Research Studentship - Internally Allocated

Cite this

@article{834ed51271c74bc9acd9c5d3a6347097,

title = "The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes",

abstract = "Coupling reactions between haloarenes and arenes (including heteroarenes) that are conducted without added transition metals but in the presence of KOtBu or NaOtBu, have been a topic of great interest since their discovery in 2008. Diverse organic structures act as additives that assist these reactions. These additives are converted into organic electron donors by the butoxide base and this leads to initiation of the coupling reactions, which proceed by radical chain mechanisms. This review provides an overview of the initiation stages of these reactions.",

keywords = "organic electron donor, benzyne, BHAS coupling, electron transfer, potassium tert-butoxide",

author = "Smith, {Andrew J.} and Poole, {Darren L.} and Murphy, {John A.}",

year = "2019",

month = nov,

day = "30",

doi = "10.1007/s11426-019-9611-x",

language = "English",

volume = "62",

pages = "1425--1438",

journal = "Science China Chemistry",

issn = "1674-7291",

number = "11",

}

TY - JOUR

T1 - The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes

AU - Smith, Andrew J.

AU - Poole, Darren L.

AU - Murphy, John A.

PY - 2019/11/30

Y1 - 2019/11/30

N2 - Coupling reactions between haloarenes and arenes (including heteroarenes) that are conducted without added transition metals but in the presence of KOtBu or NaOtBu, have been a topic of great interest since their discovery in 2008. Diverse organic structures act as additives that assist these reactions. These additives are converted into organic electron donors by the butoxide base and this leads to initiation of the coupling reactions, which proceed by radical chain mechanisms. This review provides an overview of the initiation stages of these reactions.

AB - Coupling reactions between haloarenes and arenes (including heteroarenes) that are conducted without added transition metals but in the presence of KOtBu or NaOtBu, have been a topic of great interest since their discovery in 2008. Diverse organic structures act as additives that assist these reactions. These additives are converted into organic electron donors by the butoxide base and this leads to initiation of the coupling reactions, which proceed by radical chain mechanisms. This review provides an overview of the initiation stages of these reactions.

KW - organic electron donor

KW - benzyne

KW - BHAS coupling

KW - electron transfer

KW - potassium tert-butoxide

U2 - 10.1007/s11426-019-9611-x

DO - 10.1007/s11426-019-9611-x

M3 - Article

SN - 1674-7291

VL - 62

SP - 1425

EP - 1438

JO - Science China Chemistry

JF - Science China Chemistry

IS - 11

ER -

The role of organic electron donors in the initiation of BHAS base-induced coupling reactions between haloarenes and arenes

Abstract

Keywords

Access to Document

Fingerprint

Projects

Industrial Case Account 2015 / S151217-105

Cite this