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Synthesis of Cyclobutenes and Allenes by Cobalt‐Catalyzed Cross‐Dimerization of Simple Alkenes with 1,3‐Enynes
Author(s) -
Nishimura Akira,
Tamai Eri,
Ohashi Masato,
Ogoshi Sensuke
Publication year - 2014
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.201402218
Subject(s) - regioselectivity , catalysis , chemistry , allylic rearrangement , cycloaddition , cobalt , simple (philosophy) , alkene , combinatorial chemistry , medicinal chemistry , organic chemistry , philosophy , epistemology
Cobalt‐catalyzed cross‐dimerization of simple alkenes with 1,3‐enynes is reported. A [2+2] cycloaddition reaction occurred, with alkenes bearing no allylic hydrogen, by reductive elimination of a η 3 ‐butadienyl cobaltacycle. On the other hand, aliphatic alkenes underwent 1,4‐hydroallylation by means of exo ‐cyclic β‐H elimination. These reactions can provide cyclobutenes and allenes that were previously difficult to access, from simple substrates in a highly chemo‐ and regioselective manner.