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Regioselective Heterodimerization of Styrenes with Diarylethene and Vinylnaphthalene by a Catalyst System Consisting of Simple Acid and a Ketone
Author(s) -
Fehn Sonja,
Schwarz Stefan,
Kempe Rhett
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700595
Subject(s) - regioselectivity , catalysis , ketone , chemistry , styrene , organic chemistry , combinatorial chemistry , double bond , polymer , copolymer
Selective C−C bond formation reactions based on olefins are highly important, because olefins are an inexpensive abundantly available feedstock. The development of selective but simple inexpensive catalyst systems is similarly important, since many C−C bond formation reactions are mediated by rare and expensive metal catalysts. We report here on an inexpensive metal‐free catalyst system for the regioselective heterodimerization of olefins. The key is the combination of a simple acid and a ketone as the catalyst. In addition to the homodimerization of styrene derivatives, the regioselective heterodimerization of styrene derivatives with diphenylethene and vinylnaphthalene is demonstrated. Moreover, a mechanistic proposal for the reactions discussed here is provided. We expect that our findings will inspire others to look for metal‐free catalyst systems for selective C−C bond formation reactions.