Halogen-Adjusted Chemoselective Synthesis of Fluorene Derivatives with Position-Controlled Substituents

Juan Song; Wei Sun; Yali Li; Fuliang Wei; Chao Liu; Yan Qian; Shufen Chen

doi:10.1002/asia.201501135

Halogen-Adjusted Chemoselective Synthesis of Fluorene Derivatives with Position-Controlled Substituents

Chem Asian J. 2016 Jan;11(2):211-5. doi: 10.1002/asia.201501135. Epub 2015 Nov 9.

Authors

Juan Song¹, Wei Sun², Yali Li², Fuliang Wei², Chao Liu³, Yan Qian², Shufen Chen²

Affiliations

¹ Key Laboratory for Organic Electronics and Information Displays, Institute of Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing, 210023, P. R. China. iamjsong@njupt.edu.cn.
² Key Laboratory for Organic Electronics and Information Displays, Institute of Advanced Materials, Nanjing University of Posts and Telecommunications, Nanjing, 210023, P. R. China.
³ State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou, 730000, P. R. China. chaoliu@licp.cas.cn.

PMID: 26488213
DOI: 10.1002/asia.201501135

Abstract

Fluorenes have been synthesized through an efficient novel Pd-catalyzed tandem cross-coupling reaction; these substrates are fascinating building blocks found in organic photoelectric materials. The position of the substituent on fluorenes could be conveniently tuned by changing the halogen in the ortho-halobenzyl bromide substrates when coupled with various arylboronic acids. This newly developed synthetic approach could achieve the potential diversity in fluorene-based molecular architectures.

Keywords: C−H functionalization; Palladium; chemoselectivity; cross-coupling; fluorenes.