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One‐Pot Synthesis of Unsymmetrical 1,3‐Butadiyne Derivatives and their Application in the Synthesis of Unsymmetrical 2,5‐Diarylthiophenes
Author(s) -
Andrade Camila B.,
Carvalho Diego B.,
Trefzger Ozildéia S.,
Kassab Najla M.,
Guerrero Palimécio G.,
Barbosa Sandro L.,
Shiguemoto Cristiane Y. K.,
Baroni Adriano C. M.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801242
Subject(s) - chemistry , sonogashira coupling , toluene , aryl , combinatorial chemistry , substrate (aquarium) , coupling reaction , one pot synthesis , reaction conditions , solvent , catalysis , organic chemistry , medicinal chemistry , palladium , alkyl , oceanography , geology
A one‐pot protocol was developed for the synthesis of unsymmetrical 1,3‐butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C–C(Me) 2 OH derivatives in a retro‐Favorskii reaction to furnish a terminal 1,3‐butadiyne compound, which reacted with aryl iodides in a Sonogashira‐type cross‐coupling reaction catalyzed by Pd(PPh 3 ) 4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocyclization of 1,3‐butadiynes, leading to unsymmetrical 2,5‐diarylthiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.