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A Vinyl‐Cation‐Induced 1,3‐Aryl Shift
Author(s) -
Fu Liang,
Damsen Helena,
Niggemann Meike
Publication year - 2017
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.201701255
Subject(s) - aryl , chemistry , polymer chemistry , organic chemistry , alkyl
A net insertion of an unactivated, internal alkyne into a sp 2 –sp 3 C−C bond of simple benzylic alcohols was achieved using the rearrangement of a highly reactive vinyl cation intermediate to a stabilized allyl cation as the driving force for an unusual 1,3‐carbon shift reaction. In the presence of 10 mol % of Al(OTf) 3 as a simple, inexpensive, and abundant catalyst, high selectivity for the rearrangement was achieved. The reaction scope proved general with regard to both the alkyne and the benzylic alcohol and a range of 1,2‐dihydroquinolines as well as 2 H ‐chromenes were obtained.