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Different Selectivities in the Insertions into C(sp 2 )−H Bonds: Benzofulvenes by Dual Gold Catalysis Competition Experiments
Author(s) -
Plajer Alex J.,
Ahrens Lukas,
Wieteck Marcel,
Lustosa Danilo M.,
Babaahmadi Rasool,
Yates Brian,
Ariafard Alireza,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2018
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.201801031
Subject(s) - chemoselectivity , intramolecular force , selectivity , chemistry , catalysis , aryl , combinatorial chemistry , competition (biology) , medicinal chemistry , stereochemistry , organic chemistry , alkyl , ecology , biology
An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp 2 )−H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C−H positions. A bidirectional synthesis with two competing ortho ‐aryl C−H bonds in the selectivity‐determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non‐equivalent aryl C−H bonds with a benzylic methyl group also showed perfect selectivity.