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Bromide as the Directing Group for β-Arylation of Thiophenes

Journal Article · · Synthesis
DOI:https://doi.org/10.1055/a-1838-8958· OSTI ID:1885340
 [1];  [1];  [1];  [1];  [1];  [1];  [1];  [2]
  1. Nanjing Tech University (China)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
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Direct β-arylation of thiophene derivatives with bromide as directing group is disclosed. The reaction is conducted with PdCl2/(p-tolyl)3P as catalyst, silver carbonate as additive, and aryl iodide as coupling partner, affording brominated biaryl compounds as product. Control experiments indicated that the presence of bromide group enhances the reactivity of the C–H bond, enabling β-arylation. Additionally, the C–Br bond can be easily converted into many useful functional groups through a wide range of methodologies. The mechanistic study suggests that silver salt plays a key role in the C–H bond-activation step.
Research Organization:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
Sponsoring Organization:
National Natural Science Foundation of China (NSFC); USDOE Office of Science (SC), Biological and Environmental Research (BER)
Grant/Contract Number:
AC05-00OR22725
OSTI ID:
1885340
Journal Information:
Synthesis, Journal Name: Synthesis Journal Issue: 18 Vol. 54; ISSN 0039-7881
Publisher:
ThiemeCopyright Statement
Country of Publication:
United States
Language:
English

References (5)

Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise Difficult C4-Selective CH Arylation Enabled by Boronic Acids journal January 2011
Pd/C as a Catalyst for Completely Regioselective CH Functionalization of Thiophenes under Mild Conditions journal January 2014
Transient-Ligand-Enabled ortho -Arylation of Five-Membered Heterocycles: Facile Access to Mechanochromic Materials journal February 2018
Completely Regioselective Direct C–H Functionalization of Benzo[b]thiophenes Using a Simple Heterogeneous Catalyst journal May 2013
Pd-Catalyzed β-Selective Direct C–H Bond Arylation of Thiophenes with Aryltrimethylsilanes journal December 2012

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Related Subjects

36 MATERIALS SCIENCE
bromide
silver
thiophene
β-arylation