Different Selectivities in the Insertions into C(sp2 )-H Bonds: Benzofulvenes by Dual Gold Catalysis Competition Experiments

Chemistry : a European Journal
Alex J PlajerA Stephen K Hashmi

Abstract

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.

References

May 12, 2005·Chemical Reviews·Michael E Jung, Grazia Piizzi
Nov 30, 2006·Angewandte Chemie·A Stephen K Hashmi, Graham J Hutchings
Apr 13, 2007·Angewandte Chemie·Alois Fürstner, Paul W Davies
Feb 14, 2008·Angewandte Chemie·Nadine Bongers, Norbert Krause
Jul 20, 2012·Angewandte Chemie·Adrián Gómez-Suárez, Steven P Nolan
Sep 19, 2012·Angewandte Chemie·A Stephen K HashmiFrank Rominger
May 9, 2013·Chemistry : a European Journal·Pascal NöselA Stephen K Hashmi
Jan 21, 2014·Chemistry : a European Journal·Mie Højer Vilhelmsen, A Stephen K Hashmi
Oct 10, 2014·Chemistry : a European Journal·Marcel WieteckA Stephen K Hashmi
Apr 25, 2015·Angewandte Chemie·Robert J Harris, Ross A Widenhoefer
Aug 11, 2015·Journal of the American Chemical Society·Mie Højer LarsenA Stephen K Hashmi
Dec 18, 2015·Chemical Society Reviews·Daniel Pflästerer, A Stephen K Hashmi
Feb 10, 2017·Chemistry : a European Journal·Svetlana TšupovaA Stephen K Hashmi
Feb 15, 2017·Angewandte Chemie·Thomas WurmA Stephen K Hashmi
May 4, 2017·Chemistry : a European Journal·Svetlana TšupovaA Stephen K Hashmi
Aug 2, 2017·Chemical Society Reviews·Jin XieA Stephen K Hashmi
Sep 19, 2017·Chemistry : a European Journal·Johannes E M N KleinA Stephen K Hashmi
Dec 23, 2017·Chemistry : a European Journal·Thomas WurmA Stephen K Hashmi
Jan 27, 2018·Chemistry : a European Journal·Vanessa WeingandA Stephen K Hashmi

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Citations

Sep 26, 2019·Chemical Communications : Chem Comm·Ximei ZhaoA Stephen K Hashmi
Sep 12, 2020·Chemical Society Reviews·Tahani A C A BayrakdarSteven P Nolan
Jun 13, 2020·Chemistry : a European Journal·Erik Van der Eycken, Liangliang Song
May 5, 2021·Chemistry : a European Journal·David Fabian León RayoFabien Gagosz
Apr 28, 2021·Chemistry : a European Journal·Chandrasekar PraveenVéronique Michelet

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