Enhanced Efficiency of Amide-Substituted Quinuclidine-Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins

Xiao Yang; Mengdi Ma; Meichen Xu; Yubing Pang; Haiying Zhao; Juntao Ye

doi:10.1002/cjoc.202400725

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3227 -3233. DOI: 10.1002/cjoc.202400725

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Enhanced Efficiency of Amide-Substituted Quinuclidine-Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins

Xiao Yang ¹^,²
, Mengdi Ma ¹^,²
, Meichen Xu ²
, Yubing Pang ²
, Haiying Zhao ¹^,^†
, Juntao Ye ²^,^†

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Abstract

Comprehensive Summary:An amide-substituted quinuclidine-borane has been identified as a more efficient hydridic hydrogen atom transfer (HAT) catalyst for the hydroalkylation of unactivated olefins under visible-light irradiation. ¹H NMR titration experiments reveal that the amide moiety of the quinuclidine-borane catalyst forms stronger hydrogen bonds with the carbonyl substrates, thereby improving the reaction yields. Furthermore, it was found that the reaction yields correlate well with the association constant between the quinuclidine-borane catalyst and the carbonyl substrate. A scale-up reaction using a continuous-flow photoreactor has also been demonstrated.

Keywords

Hydrogen atom transfer / Borane / Unactivated olefin / Hydroalkylation / Photocatalysis

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Xiao Yang, Mengdi Ma, Meichen Xu, Yubing Pang, Haiying Zhao, Juntao Ye. Enhanced Efficiency of Amide-Substituted Quinuclidine-Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins. Chinese Journal of Chemistry, 2024, 42(24): 3227-3233 DOI:10.1002/cjoc.202400725