Formation of Arenes via Diallylarenes Strategic Utilization of Suzuki–Miyaura Cross-Coupling, Claisen Rearrangement and Ring-Closing Metathesis.pdf

FULL PAPERS DOI: 10.1002/adsc.200600469 Formation of Arenes via Diallylarenes: Strategic Utilization of Suzuki–Miyaura Cross-Coupling, Claisen Rearrangement and Ring-Closing Metathesis a, a a Sambasivarao Kotha, * Vrajesh R. Shah, and Kalyaneswar Mandal a Department of Chemistry, Indian Institute of Technology – Bombay, Powai, Mumbai – 400076, India Fax: (+ 91)-22-2572-3480; phone: (+ 91)-22-2576-7160; e-mail: srk@chem.iitb.ac.in Received: September 12, 2006 Abstract: Two new synthetic strategies for benzoan- quence to deliver 2-substituted naphthalenes. In the nulation are reported. The first strategy is based on second strategy, a double Claisen rearrangement and the Suzuki–Miyaura cross-coupling reaction. To this RCM protocol have been used as key steps to give end, various ortho-diallylbenzene derivatives were highly functionalized benzoannulated quinone deriv- prepared from the corrresponding diiodo derivatives atives. by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were sub- Keywords: benzoannulation; Claisen rearrangement; jected to a ring-closing metathesis (RCM) and one- diallylarenes; 2-naphthalene derivatives; ring-closing pot dichlorodicyanoquinone (DDQ) oxidation se- metathesis; Suzuki–Miyaura cross-coupling Introduction As part of a major program involving metathesis sequence