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Palladium‐Catalyzed Direct Diarylation of 2‐Benzyl‐1,2,3‐triazole: a Simple Access to 4‐Aryl‐ or 4,5‐Diaryl‐2‐benzyl‐1,2,3‐triazoles and Phenanthro[9,10‐ d ][1,2,3]triazoles
Author(s) -
Shi Xinzhe,
Zhang Jian,
Roisnel Thierry,
Soulé JeanFrançois,
Doucet Henri
Publication year - 2021
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.202100324
Subject(s) - chemistry , palladium , aryl , catalysis , intramolecular force , combinatorial chemistry , medicinal chemistry , 1,2,3 triazole , reactivity (psychology) , triazole , phosphine , organic chemistry , alkyl , medicine , alternative medicine , pathology
The reactivity of 2‐benzyl‐1,2,3‐triazole in palladium‐catalyzed direct arylation was studied. The reaction conditions for the selective synthesis of 2‐benzyl‐4‐aryl‐1,2,3‐triazoles in moderate to high yields using phosphine‐free Pd(OAc) 2 catalyst and inexpensive KOAc base have been found. Then, from these 4‐aryl‐1,2,3‐triazoles, the palladium‐catalyzed C−H bond functionalization of the C5‐position allowed the synthesis of the corresponding 4,5‐diarylated 2‐benzyl‐1,2,3‐triazoles. This selective 4,5‐diarylation of 2‐benzyl‐1,2,3‐triazole was successfully applied for the straightforward building of the π ‐extended polycyclic heteroaromatic structures phenanthro[9,10‐ d ][1,2,3]triazoles through Pd‐catalyzed C4‐ and C5‐intermolecular arylations followed by Pd‐catalyzed C−H intramolecular arylation.