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Updated: May 15, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Pd-Catalyzed Selective Arylative Cascade Cyclization of 1,6-Diynes and Dibenzoxaborins for Fused Naphthalene
Muniganti Naveen Kumar1,2, Shivunapuram Mahesh1,2, Jagadeesh Babu Nanubolu2,3
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Abstract:
A palladium-catalyzed new mode of cascade arylative cyclization of 1,6-diynes is disclosed using dibenzoxaborin as an arylating agent featuring transmetalation and selective migratory insertion as the key steps. This process enables the efficient construction of polysubstituted fused naphthalene skeletons via the formation of three new C-C bonds through dual regioselectivity in both arylation as well as C-H functionalization. Some control experiments and kinetic isotope effect (KIE) studies were conducted to elucidate the reaction mechanism, and some product diversifications were achieved to showcase the synthetic potential.
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