Premium
Oxidation of Propargylic Alcohols with a 2‐Quinoxalinol Salen Copper(II) Complex and tert ‐Butyl Hydroperoxide
Author(s) -
Weerasiri Kushan C.,
Gorden Anne E. V.
Publication year - 2013
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.201201394
Subject(s) - chemistry , catalysis , copper , yield (engineering) , methylene , alcohol oxidation , tert butyl hydroperoxide , selectivity , alkyl , triple bond , medicinal chemistry , organic chemistry , combinatorial chemistry , double bond , materials science , metallurgy
The copper(II) complex of 2‐quinoxalinol salen (salqu) is an efficient catalyst for the selective oxidation of propargylic alcohols to yield the corresponding α,β‐acetylenic carbonyl compounds when used in combination with the oxidant tert ‐butyl hydroperoxide (TBHP). Excellent yields (up to 99 %) are achieved for a variety of propargylic alcohols within 1 h of reaction time. The (salqu)copper(II) complex with TBHP can be used with propargylic alcohols that contain alkyl groups in the α‐position, which can be difficult to oxidize selectively with other commonly available methods. By using this catalytic protocol, excellent selectivity was also achieved for the oxidation of propargylic alcohols over that of isolated hydroxy groups, triple bonds, or propargylic methylene groups.