The electrochemical cyclization of o-halosubstituted homoallyl ethers to indan rings

ORGN 120

Ram S. Mohan, rmohan@iwu.edu1, Eric D. Bell2, Ashvin R. Baru2, Sandra Olivero3, Rodolphe Perriot3, and Elisabet Dunach, Elisabet.Dunach-Clinet@unice.fr3. (1) Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, 201 East Beecher Street, Bloomington, IL 61701, (2) Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, 201 East Beecher Street, Bloomington, IL 61701, (3) Laboratoire Arômes, Synthèses et Interactions et Laboratoire de Chimie Bioorganique, Université de Nice-Sophia Antipolis, Nice, France, Nice, France
Homoallyl ethers are useful starting materials for the synthesis of a variety of organic molecules. We have developed an efficient synthesis of indan skeletons by a Ni(II)-catalyzed electrochemical cyclization of o-halosubstituted homoallyl ethers. The homoallyl ethers are synthesized from the corresponding aldehydes either via the acetal or by a one-pot method, which involves in situ generation of the acetal. We have demonstrated that bismuth(III) triflate is an efficient catalyst for the synthesis of homoallyl ethers from aldehydes. Bismuth compounds are attractive as catalysts because they are remarkably non-toxic and easy to handle.