Synthesis 2017; 49(15): 3407-3421
DOI: 10.1055/s-0036-1588493
short review
© Georg Thieme Verlag Stuttgart · New York

Direct C–H Functionalization of Heteroarenes via Redox-Neutral Radical Process: A Facile Route to C–C Bonds Formation

Pin Gao
Department of Chemistry, School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi’an Jiaotong University, Xi’an 710049, P. R. of China   Email: duanxh@xjtu.edu.cn
,
Yu-Rui Gu
Department of Chemistry, School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi’an Jiaotong University, Xi’an 710049, P. R. of China   Email: duanxh@xjtu.edu.cn
,
Xin-Hua Duan*
Department of Chemistry, School of Science and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi’an Jiaotong University, Xi’an 710049, P. R. of China   Email: duanxh@xjtu.edu.cn
› Author Affiliations
Financial support from the Natural Science Basic Research Plan in Shaanxi Province of China (No. 2016JZ002) and the Fundamental Research Funds of the Central Universities (No. 2015qngz17 and xjj2016056) is greatly appreciated.
Further Information

Publication History

Received: 04 May 2017

Accepted after revision: 16 June 2017

Publication Date:
06 July 2017 (eFirst)

Abstract

Aromatic heterocycles are an important class of compounds found in a wide range of natural products, pharmaceutically active molecules and organic materials. Recently, the direct radical functionalization of heteroaromatic C–H bonds has become an efficient and attractive method to access substituted heteroarenes. Especially, redox-neutral radical reactions have attracted much attention of chemists due to their potential advantages such as mild conditions, free of external oxidants, and good functional group tolerance. So far, a series of redox-neutral radical reactions have been developed. In this review, we mainly focus on the recent advance in direct redox-neutral radical C–H functionalization of heteroarenes. Herein, the direct C–H arylation, C–H alkylation, and C–H fluoroalkylation of heteroarenes are represented respectively, providing practical routes to C–C bond formation.

1 Introduction

2 C–H Arylation of Heteroarenes with Aryl Radicals

3 C–H Alkylation of Heteroarenes with Alkyl Radicals

4 C–H Fluoroalkylation of Heteroarenes with Fluorine-Containing Carbon Radicals

5 Concluding Remarks

 
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