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Synthesis 2018; 50(15): 2908-2914
DOI: 10.1055/s-0036-1592000
special topic
© Georg Thieme Verlag Stuttgart · New York

Irradiation-Induced Palladium-Catalyzed Direct C–H Alkylation of Heteroarenes with Tertiary and Secondary Alkyl Bromides

Guang-Zu Wang
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
,
Rui Shang  *
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
b   Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Email: rui@chem.s.u-tokyo.ac.jp
,
Yao Fu*
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
› Author AffiliationsThis work was supported by NSFC (21325208, 21572212), MOST (2017YFA0303500), FRFCU, PCSIRT, and KY (2060000019).
Further Information

Publication History

Received: 28 February 2018

Accepted after revision: 03 April 2018

Publication Date:
25 April 2018 (online)

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

A palladium catalyst in combination with two types of phosphine ligands efficiently catalyzes direct C–H alkylation of heteroarenes with secondary and tertiary alkyl bromides under irradiation conditions. Irradiation of blue light-emitting diodes (blue LEDs) effectively excites phosphine-ligated palladium catalyst to facilitate oxidative addition with alkyl bromides, and also excites the alkylpalladium species to enable the generation of alkyl radicals to react with heteroarenes.

Key words

irradiation - palladium catalysis - alkylation - heteroarenes - alkyl bromides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1592000.
  • Supporting Information
 

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