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Oxypalladation Initiating the Oxidative Heck Reaction with Alkenyl Alcohols: Synthesis of Isocoumarin–Alkanones
Author(s) -
Zheng Meifang,
Huang Liangbin,
Tong Qizhen,
Wu Wanqing,
Jiang Huanfeng
Publication year - 2016
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.201501451
Subject(s) - isocoumarin , chemistry , regioselectivity , isocoumarins , intramolecular force , functional group , organic chemistry , catalysis , oxidative coupling of methane , medicinal chemistry , polymer
Highly regioselective nucleopalladation for the oxidative coupling of internal alkynes with alkenyl alcohols by using green and low‐costing oxygen as the sole oxidant was investigated. This one‐pot cascade cyclization proceeds through Pd‐catalyzed intramolecular C–O bond cyclization, insertion of nonbiased alkenyl alcohols, β‐H elimination, and reinsertion of a HPdX species, which is finally transferred to the target ketones. This method has the advantages of mild conditions, good functional group tolerance, and can be performed with unactivated alkenes to afford isocoumarin derivatives.