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Pd‐catalyzed bicyclization of 2‐alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans: a DFT study
Author(s) -
Yang Liu,
Ren Gerui,
Ye Xinchen,
Que Xianyong,
Lei Qunfang,
Fang Wenjun,
Xie Hujun
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3271
Subject(s) - chemistry , reductive elimination , catalysis , catalytic cycle , oxidative addition , triple bond , density functional theory , computational chemistry , medicinal chemistry , ligand (biochemistry) , oxidative phosphorylation , combinatorial chemistry , double bond , organic chemistry , biochemistry , receptor
The mechanism of palladium‐catalyzed bicyclization of 2‐alkynylhalobenzenes and propargylic alcohols for the formation of indeno[1,2]furans has been studied computationally with the aid of density functional theory (DFT). Full free energy profiles are computed for different reaction equations between different reaction substrates. The calculation results showed that the catalytic cycle is found to contain six steps, oxidative addition , ligand substitution, first C ≡ C triple bond insertion, rearrangement , second C ≡ C triple bond insertion and reductive elimination, with the reductive elimination being the rate‐determining step for the different reaction equations (1), (2) and (3). Our calculations are consistent with experimental observations. Copyright © 2014 John Wiley & Sons, Ltd.