Open AccessTri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes
Author(s) -
Govdi Anastasiya I.,
Vasilevsky Sergey F.,
Malysheva Svetlana F.,
Kazheva Olga N.,
Dyachenko Oleg A.,
Kuimov Vladimir A.
Publication year - 2018
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.21443
Subject(s) - sonogashira coupling , chemistry , phosphine , aryl , palladium , ligand (biochemistry) , yield (engineering) , phosphorus , medicinal chemistry , coupling (piping) , coupling reaction , organic chemistry , combinatorial chemistry , catalysis , receptor , metallurgy , alkyl , biochemistry , materials science
Tri(1‐naphthyl)phosphine (Np 3 P) has been easily prepared in 34% yield from red phosphorus and 1‐bromonaphthalene in the superbasic system t ‐Bu ON a/ DMSO . The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np 3 P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron‐donating substituents preferably affords buta‐1,3‐diynes.