Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes

Shengze Zhou, Eswararao Doni, Greg M. Anderson, Ryan G. Kane, Scott W. MacDougall, Victoria M. Ironmonger, Tell Tuttle, John A. Murphy

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KO(t)Bu or NaO(t)Bu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.
LanguageEnglish
Pages17818-17826
Number of pages9
JournalJournal of the American Chemical Society
Volume136
Issue number51
Early online date4 Dec 2014
DOIs
Publication statusPublished - 24 Dec 2014

Fingerprint

Amino Alcohols
Diamines
Amino acids
Alcohols
Electrons
Amino Acids
Experiments

Keywords

  • organic electron donors
  • organic additives
  • haloarenes
  • arenes

Cite this

Zhou, Shengze ; Doni, Eswararao ; Anderson, Greg M. ; Kane, Ryan G. ; MacDougall, Scott W. ; Ironmonger, Victoria M. ; Tuttle, Tell ; Murphy, John A. / Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 51. pp. 17818-17826.
@article{40b845d7acda425f9cf38c516889b3df,
title = "Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes",
abstract = "Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KO(t)Bu or NaO(t)Bu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.",
keywords = "organic electron donors, organic additives, haloarenes, arenes",
author = "Shengze Zhou and Eswararao Doni and Anderson, {Greg M.} and Kane, {Ryan G.} and MacDougall, {Scott W.} and Ironmonger, {Victoria M.} and Tell Tuttle and Murphy, {John A.}",
year = "2014",
month = "12",
day = "24",
doi = "10.1021/ja5101036",
language = "English",
volume = "136",
pages = "17818--17826",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "51",

}

Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes. / Zhou, Shengze; Doni, Eswararao; Anderson, Greg M.; Kane, Ryan G.; MacDougall, Scott W.; Ironmonger, Victoria M.; Tuttle, Tell; Murphy, John A.

In: Journal of the American Chemical Society, Vol. 136, No. 51, 24.12.2014, p. 17818-17826.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Identifying the roles of amino acids, alcohols and 1,2-diamines as mediators in coupling of haloarenes to arenes

AU - Zhou, Shengze

AU - Doni, Eswararao

AU - Anderson, Greg M.

AU - Kane, Ryan G.

AU - MacDougall, Scott W.

AU - Ironmonger, Victoria M.

AU - Tuttle, Tell

AU - Murphy, John A.

PY - 2014/12/24

Y1 - 2014/12/24

N2 - Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KO(t)Bu or NaO(t)Bu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.

AB - Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KO(t)Bu or NaO(t)Bu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.

KW - organic electron donors

KW - organic additives

KW - haloarenes

KW - arenes

UR - http://pubs.acs.org/journal/jacsat

U2 - 10.1021/ja5101036

DO - 10.1021/ja5101036

M3 - Article

VL - 136

SP - 17818

EP - 17826

JO - Journal of the American Chemical Society

T2 - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 51

ER -