Enantioselective Hydrogenation of Benzofurans with Water via Rh/Hf Cooperative Catalysts: Convenient Access to Chiral 2,3-Dihydrobenzofurans

Hekun Yang; Devendar Ponnam; Xiong Tao; Qiongtong Yang; Jingchao Chen; Baomin Fan

doi:10.1002/cjoc.70249

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (24) :3429 -3436. DOI: 10.1002/cjoc.70249

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Enantioselective Hydrogenation of Benzofurans with Water via Rh/Hf Cooperative Catalysts: Convenient Access to Chiral 2,3-Dihydrobenzofurans

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Abstract

The chiral 2,3-dihydrobenzofuran (DHB) scaffold is a privileged motif in bioactive natural products and preclinical therapeutic candidates, yet practical enantioselective syntheses remain scarce. We report a chiral Rh/Hf/(S)-DTBM-SEGPHOS bimetallic catalytic system enabling asymmetric hydrogenation of benzofurans with hydrogen source, delivering diverse DHBs (37 examples) in excellent yields (up to 98%) and enantioselectivities (up to 99% ee). Gram-scale synthesis and deuterium labeling with D₂O (8 examples) validate the method's scalability and utility in biological studies and drug design.

Keywords

Asymmetric catalysis / Hydrogenation / Deuteration / Benzofuran / Dihydrobenzofuran

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Hekun Yang, Devendar Ponnam, Xiong Tao, Qiongtong Yang, Jingchao Chen, Baomin Fan. Enantioselective Hydrogenation of Benzofurans with Water via Rh/Hf Cooperative Catalysts: Convenient Access to Chiral 2,3-Dihydrobenzofurans. Chinese Journal of Chemistry, 2025, 43(24): 3429-3436 DOI:10.1002/cjoc.70249