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Direct Synthesis of Protoberberine Alkaloids by Rh‐Catalyzed C−H Bond Activation as the Key Step
Author(s) -
Jayakumar Jayachandran,
Cheng ChienHong
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504378
Subject(s) - catalysis , chemistry , key (lock) , stereochemistry , combinatorial chemistry , organic chemistry , biology , ecology
A one‐pot reaction of substituted benzaldehydes with alkyne–amines by a Rh‐catalyzed C−H activation and annulation to afford various natural and unnatural protoberberine alkaloids is reported. This reaction provides a convenient route for the generation of a compound library of protoberberine salts, which recently have attracted great attention because of their diverse biological activities. In addition, pyridinium salt derivatives can also be formed in good yields from α,β‐unsaturated aldehydes and amino–alkynes. This reaction proceeds with excellent regioselectivity and good functional group compatibility under mild reaction conditions by using O 2 as the oxidant.