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Design and Synthesis of Camphor‐derived Chiral [1,2,4]Triazolo[4,3‐ a ]tetrahydroquinoline N‐Heterocyclic Carbene Precursors by Pd‐Catalyzed Coupling Reactions of Aryl Hydrazides with a Pyridyl Triflate Derivative
Author(s) -
Chen LiangAn,
Wang ChuanFei,
Lin MingGui,
Zhang JinLong,
Huang PeiQiang,
Wang AiE
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300024
Subject(s) - carbene , chemistry , camphor , aryl , trifluoromethanesulfonate , phosphine , medicinal chemistry , catalysis , ligand (biochemistry) , coupling reaction , combinatorial chemistry , organic chemistry , stereochemistry , alkyl , biochemistry , receptor
Which came first? A Pd‐catalyzed coupling reaction of N‐ tert ‐butyloxycarbonyl (Boc) aryl hydrazines with a camphor‐derived pyridyl triflate derivative has been developed by using bulky electron‐rich phosphine or N‐heterocyclic carbene as the ligand. With this CN coupling reaction as the key step, camphor‐derived chiral [1,2,4]triazolo[4,3‐ a ]tetrahydroquinoline N‐heterocyclic carbene precursors were synthesized. Tf=trifluoromethanesulfonyl.