Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles

作者：Wang Bi, Jing-Kun Gao, Shuo Sun, Zhenlu Shen, Yun‐Fang Yang, Ren‐Xiao Liang, Yi‐Xia Jia · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.4c00775 · 被引用次数：21 · 研究领域：Catalytic C–H Functionalization Methods、Asymmetric Hydrogenation and Catalysis、Catalytic Cross-Coupling Reactions

An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of N -( o -bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba) 2 /SPINOL-based phosphoramidite as the chiral catalyst and HCO 2 Na as the hydride source, a series of enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The reductive Heck reaction of formal tetrasubstituted alkene bearing β-hydrogens is therefore realized by inhibiting β-H elimination.