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Construction of Alkenyl‐Functionalized Spirocarbocyclic Scaffolds from Alkyne‐Containing Phenol‐Based Biaryls via Sequential Iodine‐Induced Cyclization/Dearomatization and Pd‐Catalyzed Coupling of N ‐Tosylhydrazones
Author(s) -
Liu Anjia,
Han Kaiming,
Wu XinXing,
Chen Shufeng,
Wang Jianbo
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000170
Subject(s) - chemistry , alkyne , phenol , catalysis , iodine , steric effects , combinatorial chemistry , halide , organic chemistry
Summary of main observation and conclusion An efficient strategy for the formation of alkenyl‐functionalized spirocarbocyclic scaffolds from alkyne‐containing phenol‐based biaryls via sequential iodine‐induced cyclization/dearomatization and Pd‐catalyzed coupling of N ‐tosylhydrazones is developed. The approach provides various spirocarbocyclic compounds in moderate to excellent yields with good functional tolerance. The results also demonstrate the feasibility for the direct cross‐couplings of N ‐tosylhydrazones with sterically congested tetrasubstituted alkenyl halides.