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(sp²)-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.

Item Type:	Refereed Article
Keywords:	density functional theory, mechanistic elucidation, C-H insertion, chemoselectivity, dual gold catalysis, gold vinylidenes
Research Division:	Chemical Sciences
Research Group:	Inorganic chemistry
Research Field:	Organometallic chemistry
Objective Division:	Expanding Knowledge
Objective Group:	Expanding knowledge
Objective Field:	Expanding knowledge in the chemical sciences
UTAS Author:	Babaahmadi, R (Mr Rasool Babaahmadi)
UTAS Author:	Yates, B (Professor Brian Yates)
UTAS Author:	Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:	128286
Year Published:	2018
Funding Support:	Australian Research Council (DP180100904)
Web of Science® Times Cited:	20
Deposited By:	Chemistry
Deposited On:	2018-09-12
Last Modified:	2022-08-18
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