Strategic combination of Suzuki-Miyaura cross-coupling and olefin metathesis for benzoannulation strategy and synthesis of 1-benzazepine derivatives

ORGN 316

Sambasivarao Kotha, srk@chem.iitb.ac.in and Vrajesh R Shah, vrajesh@chem.iitb.ac.in. Department of Chemistry, Indian Institute of Technology, Powai, Mumbai, Indian Institute of Technology, Powai, Mumbai 400076, 400 076, India
Suzuki-Miyaura (SM) cross-coupling reaction is one of the most powerful tools available for the formation of carbon-carbon bond under mild reaction conditions. We have developed a simple methodology for allylation of aromatic iodides (or bromides) using allyl boronic ester 1 via the SM cross-coupling reaction. As an extension of allylation strategy, we developed a methodology for synthesis of 2-substituted naphthalene derivatives via ring-closing metathesis (RCM) sequence as a key step (Scheme 1). Also, various 1-benzazepine derivatives were prepared via RCM and intramolecular enyne metathesis as a key step (Scheme 2).

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Tuesday, March 27, 2007 McCormick Place Lakeside -- Room E350, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007