Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes | Zendy

Govdi Anastasiya I. | Zendy; Vasilevsky Sergey F. | Zendy; Malysheva Svetlana F. | Zendy; Kazheva Olga N. | Zendy; Dyachenko Oleg A. | Zendy; Kuimov Vladimir A. | Zendy

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Tri(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.

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