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Remote and Selective C(sp2)–H Olefination for Sequential Regioselective Linkage of Phenanthrenes

Authors :
Wei, Yi
Duan, Abing
Tang, Pan-Ting
Li, Jia-Wei
Peng, Rou-Ming
Zhou, Zheng-Xin
Luo, Xiao-Peng
Kurmoo, Mohamedally
Liu, Yue-Jin
Zeng, Ming-Hua
Source :
Organic Letters; June 2020, Vol. 22 Issue: 11 p4129-4134, 6p
Publication Year :
2020

Abstract

Biphenylcarboxylic acid with two competing C(sp2)-H sites was designed for site selective C(sp2)-H functionalization by developing carboxylic acids assisted remote and selective olefination via 7-membered palladacycle. Mechanism investigation and DFT calculations reveal a kinetics-determined process, which could be utilized to explore a variety of remote site selectivity. The practicability of this method was highlighted by the precise construction of phenathrene under sequential site selectivity.

Details

Language :
English
ISSN :
15237060 and 15237052
Volume :
22
Issue :
11
Database :
Supplemental Index
Journal :
Organic Letters
Publication Type :
Periodical
Accession number :
ejs53337803
Full Text :
https://doi.org/10.1021/acs.orglett.0c01208