Palladium-catalyzed [4 + 4] cycloaddition of homo-TMM all-carbon 1,4-dipole precursors for the construction of benzofu-ro[3,2-b]azocines Ying Chen,a Yang-Zi Liu,b Xiaoyan Luo*,a and Wei-Ping Deng*,b,a Chin. J. Chem. 2023, 41, XXX—XXX. DOI: 10.1002/cjoc.202300XXX
We developed a novel Pd-catalyzed [4 + 4] cycloaddition of benzofuran-derived azadienes with homo-TMM all-carbon 1,4-dipoles in situ generated from α-allyl malonate derivatives, affording an array of benzofuro[3,2-b]azocines with good to excellent yields (up to 96%) and exclusive regioselectivities. This methodology featured mild reaction conditions and good functional group tolerance. The synthetic utility was demonstrated by a gram-scale reaction. Furthermore, the catalytic asymmetric [4 + 4] cycloaddition version has also been explored.