Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water

Ksenia V. Kutonova, Nicole Jung, Marina E. Trusova, Victor D. Filimonov, Pavel S. Postnikov, Stefan Bräse

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling­ was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.

Original languageEnglish
Article numberss-2016-z0633-op
Pages (from-to)1680-1688
Number of pages9
JournalSynthesis (Germany)
Volume49
Issue number7
DOIs
Publication statusPublished - 1 Apr 2017

Fingerprint

Boron Compounds
Boron compounds
Functional groups
Water
palladium(II) acetate

Keywords

  • arenediazonium salts
  • arenediazonium tosylates
  • biphenyls
  • Suzuki-Miyaura reactions
  • water media

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water. / Kutonova, Ksenia V.; Jung, Nicole; Trusova, Marina E.; Filimonov, Victor D.; Postnikov, Pavel S.; Bräse, Stefan.

In: Synthesis (Germany), Vol. 49, No. 7, ss-2016-z0633-op, 01.04.2017, p. 1680-1688.

Research output: Contribution to journalArticle

@article{7d0b997bea0a400794962bb92b800886,
title = "Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water",
abstract = "A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling­ was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.",
keywords = "arenediazonium salts, arenediazonium tosylates, biphenyls, Suzuki-Miyaura reactions, water media",
author = "Kutonova, {Ksenia V.} and Nicole Jung and Trusova, {Marina E.} and Filimonov, {Victor D.} and Postnikov, {Pavel S.} and Stefan Br{\"a}se",
year = "2017",
month = "4",
day = "1",
doi = "10.1055/s-0036-1588919",
language = "English",
volume = "49",
pages = "1680--1688",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "7",

}

TY - JOUR

T1 - Arenediazonium Tosylates (ADTs) as Efficient Reagents for Suzuki-Miyaura Cross-Coupling in Neat Water

AU - Kutonova, Ksenia V.

AU - Jung, Nicole

AU - Trusova, Marina E.

AU - Filimonov, Victor D.

AU - Postnikov, Pavel S.

AU - Bräse, Stefan

PY - 2017/4/1

Y1 - 2017/4/1

N2 - A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling­ was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.

AB - A simple, convenient, and environment-friendly procedure for the preparation of substituted biaryls via Suzuki-Miyaura cross-coupling­ was developed. The use of arenediazonium tosylates and corresponding boron compounds allows a conversion in neat water in the presence of commercially available Pd(OAc)2 under mild conditions with tolerance to a wide range of functional groups. A procedure particularly useful for the synthesis of di-ortho-substituted biaryls was developed.

KW - arenediazonium salts

KW - arenediazonium tosylates

KW - biphenyls

KW - Suzuki-Miyaura reactions

KW - water media

UR - http://www.scopus.com/inward/record.url?scp=85000671364&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85000671364&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1588919

DO - 10.1055/s-0036-1588919

M3 - Article

VL - 49

SP - 1680

EP - 1688

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 7

M1 - ss-2016-z0633-op

ER -