Selective reduction of carboxylic acids to aldehydes with hydrosilane via photoredox catalysis

被引:33
|
作者
Zhang, Muliang [1 ]
Li, Nan [1 ]
Tao, Xingyu [1 ]
Ruzi, Rehanguli [1 ]
Yu, Shouyun [1 ]
Zhu, Chengjian [1 ,2 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat, Nanjing 210093, Jiangsu, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
REPRESENTATIVE FUNCTIONAL-GROUPS; ALPHA-KETO ACIDS; DECARBOXYLATIVE ALKYNYLATION; CHEMOSELECTIVE CONVERSION; CORRESPONDING ALDEHYDES; MERGING PHOTOREDOX; HYDRIDE REDUCTIONS; ORGANIC-COMPOUNDS; DIMETHYL SULFIDE; FACILE REDUCTION;
D O I
10.1039/c7cc05570f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct reduction of carboxylic acids to aldehydes with hydrosilane was achieved through visible light photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps offers a novel and convenient approach to selective reduction of carboxylic acids to aldehydes. The method also features mild conditions, high yields, broad substrate scope, and good functional group tolerance, such as alkyne, ester, ketone, amide and amine groups.
引用
收藏
页码:10228 / 10231
页数:4
相关论文
共 50 条
  • [21] Aroyl chlorides as novel acyl radical precursors via visible-light photoredox catalysis
    Xu, Shi-Ming
    Chen, Jian-Qiang
    Liu, Dan
    Bao, Yun
    Liang, Yong-Min
    Xu, Peng-Fei
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1331 - 1335
  • [22] Access to Alkyl-Substituted Lactone via Photoredox-Catalyzed Alkylation/Lactonization of Unsaturated Carboxylic Acids
    Sha, Wanxing
    Ni, Shengyang
    Han, Jianlin
    Pan, Yi
    ORGANIC LETTERS, 2017, 19 (21) : 5900 - 5903
  • [23] Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis
    Beil, Sebastian B.
    Chen, Tiffany Q.
    Intermaggio, Nicholas E.
    MacMillan, David W. C.
    ACCOUNTS OF CHEMICAL RESEARCH, 2022, 55 (23) : 3481 - 3494
  • [24] Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis
    Patel, Niki R.
    Kelly, Christopher B.
    Jouffroy, Matthieu
    Molander, Gary A.
    ORGANIC LETTERS, 2016, 18 (04) : 764 - 767
  • [25] Photoredox catalytic phosphine-mediated deoxygenative alkynylation of carboxylic acids with alkynyl sulfones for alkynone synthesis
    Tang, Wen-Huan
    Wu, Li-Yuan
    Zhou, Quan-Quan
    Wan, Jie-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2025, : 2340 - 2345
  • [26] Organophotoredox/Copper Hybrid Catalysis for Regioselective Allylic Aminodecarboxylation of β,γ-Unsaturated Carboxylic Acids
    Manick, Anne-Doriane
    Tanaka, Hirotaka
    Oisaki, Kounosuke
    Kanai, Motomu
    SYNTHESIS-STUTTGART, 2018, 50 (15): : 2936 - 2947
  • [27] Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis
    Wei, Lidan
    Wu, Chengjuan
    Tung, Chen-Ho
    Wang, Wenguang
    Xu, Zhenghu
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (18): : 3224 - 3227
  • [28] Visible-Light Photoredox-Catalyzed Decarboxylative Alkylation of Heteroarenes Using Carboxylic Acids with Hydrogen Release
    Tian, Wan-Fa
    Hu, Chun-Hong
    He, Ke-Han
    He, Xiao-Ya
    Li, Yang
    ORGANIC LETTERS, 2019, 21 (17) : 6930 - 6935
  • [29] Synthesis of Difluoroalkylated Arenes by Hydroaryldifluoromethylation of Alkenes with α,α-Difluoroarylacetic Acids under Photoredox Catalysis
    Yang, Bin
    Xu, Xiu-Hua
    Qing, Feng-Ling
    ORGANIC LETTERS, 2016, 18 (22) : 5956 - 5959
  • [30] Sulfonated carbon catalyzed oxidation of aldehydes to carboxylic acids by hydrogen peroxide
    Zhou, Lipeng
    Dong, Beibei
    Tang, Si
    Ma, Hong
    Chen, Chen
    Yang, Xiaomei
    Xu, Jie
    JOURNAL OF ENERGY CHEMISTRY, 2013, 22 (04) : 659 - 664