Concise Report
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,
Xiao Yang
Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorMengdi Ma
Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorMeichen Xu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorYubing Pang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Haiying Zhao
Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Juntao Ye
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]; [email protected]Search for more papers by this authorXiao Yang,
Mengdi Ma,
Meichen Xu,
Yubing Pang,
Haiying Zhao,
Juntao Ye,
Xiao Yang
Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorMengdi Ma
Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorMeichen Xu
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorYubing Pang
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
Search for more papers by this authorCorresponding Author
Haiying Zhao
Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot, Inner Mongolia, 010021 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Juntao Ye
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240 China
E-mail: [email protected]; [email protected]Search for more papers by this author†
† Dedicated to the Special Issue of Emerging Investigators in 2024.
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.
Supporting Information
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Appendix S1: Supporting Information |
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