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

doi:10.1021/ja5101036

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

Pure And Applied Chemistry

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

126 Citations (Scopus)

220 Downloads (Pure)

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.

Original language	English
Pages (from-to)	17818-17826
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	136
Issue number	51
Early online date	4 Dec 2014
DOIs	https://doi.org/10.1021/ja5101036
Publication status	Published - 24 Dec 2014

Keywords

organic electron donors
organic additives
haloarenes
arenes

Access to Document

10.1021/ja5101036Licence: CC BY 4.0

Zhou-etal-JACS2014-the-roles-of-amino-acids-alcohols-and-1-2-diaminesFinal published version, 1.5 MBLicence: CC BY 4.0
Zhou-etal-JACS2014-the-roles-of-amino-acids-alcohols-and-1-2-diamines-supplementary-infoFinal published version, 2.82 MBLicence: CC BY 4.0

Cite this

@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 = dec,

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",

}

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

C2 - 25474411

SN - 0002-7863

VL - 136

SP - 17818

EP - 17826

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 51

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

John Murphy

Light-Activated Approaches to Highly Challenging Organic Electron Transfer Reactions

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Profiles

John Murphy

Projects

Light-Activated Approaches to Highly Challenging Organic Electron Transfer Reactions

Cite this