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Divergent Palladium‐ and Platinum‐Catalyzed Intramolecular Hydroamination/Hydroarylation of O ‐Propargyl‐2‐aminophenols
Author(s) -
Christodoulou Michael S.,
Giofrè Sabrina,
Broggini Gianluigi,
Mazza Alberto,
Sala Roberto,
Beccalli Egle M.
Publication year - 2018
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.201801103
Subject(s) - hydroamination , chemistry , palladium , propargyl , catalysis , regioselectivity , intramolecular force , platinum , surface modification , combinatorial chemistry , medicinal chemistry , organic chemistry
A fruitful divergent cyclization of terminal alkynes arising from 2‐aminophenols depending on the transition metal employed is reported. Under palladium‐ and platinum‐catalysis, the total regioselective carbon–nitrogen or carbon–carbon bonds formation afforded 1,4‐benzoxazines or benzopyrans, through different reaction pathways. The subsequent functionalization of the benzopyran scaffold paved the way for a new synthesis of the tricyclic pyrano[3,2‐ h ]quinolines.