Palladium-catalyzed direct C-H arylation of enamides with simple arenes

Sreekumar Pankajakshan, Yun He Xu, Jun Kee Cheng, Man Ting Low, Teck Peng Loh

Research output: Contribution to journalArticle

Abstract

Z only: An atom-economical synthetic route towards arylated Z-enamides through double C-H functionalization is described. The Z/E selectivity of the palladium-catalyzed monoarylation is absolute (step A in scheme), and the molecular complexity of the products can be further endowed by a sequential second arylation, which requires the use of trifluoracetic acid (TFA; step B).

Original languageEnglish (US)
Pages (from-to)5701-5705
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number23
DOIs
StatePublished - Jun 4 2012

Fingerprint

Palladium
Atoms
Acids

Keywords

  • arylation
  • C-H functionalization
  • enamides
  • palladium
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Palladium-catalyzed direct C-H arylation of enamides with simple arenes. / Pankajakshan, Sreekumar; Xu, Yun He; Cheng, Jun Kee; Low, Man Ting; Loh, Teck Peng.

In: Angewandte Chemie - International Edition, Vol. 51, No. 23, 04.06.2012, p. 5701-5705.

Research output: Contribution to journalArticle

Pankajakshan, Sreekumar ; Xu, Yun He ; Cheng, Jun Kee ; Low, Man Ting ; Loh, Teck Peng. / Palladium-catalyzed direct C-H arylation of enamides with simple arenes. In: Angewandte Chemie - International Edition. 2012 ; Vol. 51, No. 23. pp. 5701-5705.
@article{6ecf960a0c6743bb85b890182432f811,
title = "Palladium-catalyzed direct C-H arylation of enamides with simple arenes",
abstract = "Z only: An atom-economical synthetic route towards arylated Z-enamides through double C-H functionalization is described. The Z/E selectivity of the palladium-catalyzed monoarylation is absolute (step A in scheme), and the molecular complexity of the products can be further endowed by a sequential second arylation, which requires the use of trifluoracetic acid (TFA; step B).",
keywords = "arylation, C-H functionalization, enamides, palladium, synthetic methods",
author = "Sreekumar Pankajakshan and Xu, {Yun He} and Cheng, {Jun Kee} and Low, {Man Ting} and Loh, {Teck Peng}",
year = "2012",
month = "6",
day = "4",
doi = "10.1002/anie.201109247",
language = "English (US)",
volume = "51",
pages = "5701--5705",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "23",

}

TY - JOUR

T1 - Palladium-catalyzed direct C-H arylation of enamides with simple arenes

AU - Pankajakshan, Sreekumar

AU - Xu, Yun He

AU - Cheng, Jun Kee

AU - Low, Man Ting

AU - Loh, Teck Peng

PY - 2012/6/4

Y1 - 2012/6/4

N2 - Z only: An atom-economical synthetic route towards arylated Z-enamides through double C-H functionalization is described. The Z/E selectivity of the palladium-catalyzed monoarylation is absolute (step A in scheme), and the molecular complexity of the products can be further endowed by a sequential second arylation, which requires the use of trifluoracetic acid (TFA; step B).

AB - Z only: An atom-economical synthetic route towards arylated Z-enamides through double C-H functionalization is described. The Z/E selectivity of the palladium-catalyzed monoarylation is absolute (step A in scheme), and the molecular complexity of the products can be further endowed by a sequential second arylation, which requires the use of trifluoracetic acid (TFA; step B).

KW - arylation

KW - C-H functionalization

KW - enamides

KW - palladium

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84861625900&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84861625900&partnerID=8YFLogxK

U2 - 10.1002/anie.201109247

DO - 10.1002/anie.201109247

M3 - Article

VL - 51

SP - 5701

EP - 5705

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 23

ER -