Lewis Acid-Catalyzed Remote Site-Selective Ring Deconstruction of Cyclobuteno[a]naphthalene-4-ones to Access Unsymmetric 1,1-Diarylated Olefins

Meng-Fan Li,¹ Ling-Qi Chen,¹ Jia-Yin Wang, Man-Su Tu,* Wen-Juan Hao,* Bo Jiang*

A catalytic site-selective ring deconstruction of cyclobuteno[a]naphthalene-4-ones with alcohols is reported, enabling the direct production of a wide range of unsymmetric 1,1-diarylated olefins with good yields and complete regioselectivity. The late-stage application of these resulting terminal olefins demonstrates great possibilities to apply this strategy to complex molecules. The protocol features good functional group compatibility, broad substrate scope and controllable site-selectivity.

J. Org. Chem. 2023, 88, 3615-3625; DOI: 10.1021/acs.joc.2c02804