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Tetraphosphine/palladium‐catalyzed Suzuki–Miyaura coupling of heteroaryl halides with 3‐pyridine‐ and 3‐thiopheneboronic acid: an efficient catalyst for the formation of biheteroaryls
Author(s) -
Wang Kun,
Fu Qi,
Zhou Rong,
Zheng Xueli,
Fu Haiyan,
Chen Hua,
Li Ruixiang
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.2965
Subject(s) - chemistry , catalysis , pyridine , halide , palladium , suzuki reaction , medicinal chemistry , ethylenediamine , organic chemistry , indole test , polymer chemistry
An easily prepared tetraphosphine N , N , N ′, N ′‐tetra(diphenylphosphinomethyl)‐1,2‐ethylenediamine (L1) associated with [Pd(η 3 ‐C 3 H 5 )Cl] 2 affords an efficient catalyst for Suzuki–Miyaura coupling of 3‐pyridineboronic acid with heteroaryl bromides. Reaction could be performed with as little as 0.02 mol% catalyst and a high turnover number of 2500 is obtained. A wide range of substrates is investigated with satisfactory yields, and good compatibility with aminogroup‐substituted pyridines and unprotected indole is exhibited. This protocol can also be applied successfully to the reaction of heteroaryl bromides with 3‐thiopheneboronic acid. This Pd‐tetraphosphine catalyst efficiently restrains the poisoning effect from heteroaryls, and shows good stability and longevity. Copyright © 2013 John Wiley & Sons, Ltd.