Photoinduced transition-metal and external photosensitizer free phosphonation of unactivated C(sp2)-F bond via SET process under mild conditions

被引：15
|
作者：
Dou, Qian [1 ]
Lang, Yatao [1 ]
Zeng, Huiying [1 ]
Li, Chao-Jun [2 ,3 ]
机构：
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[2] McGill Univ, Dept Chem, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada
[3] McGill Univ, FQRNT Ctr Green Chem & Catalysis, 801 Sherbrooke St West, Montreal, PQ H3A 0B8, Canada
来源：
FUNDAMENTAL RESEARCH | 2021年 / 1卷 / 06期
基金：
中国国家自然科学基金; 加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词：
Photochemistry; Catalyst-free; C-F bond cleavage; Phosphonation; Cross-coupling; C-F BOND; FREE N-ARYLATION; ARYL FLUORIDES; GRIGNARD-REAGENTS; ACTIVATION; FLUOROARENES; THERMOCHEMISTRY; CYCLIZATION; AMINATION; LIGAND;
D O I：
10.1016/j.fmre.2021.06.018
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
Transition-metal catalyzed cross-couplings of aryl halides (Ad, ArBr and ArCl) with a broad range of nucleophiles have been developed as powerful methods for carbon-carbon and carbon-heteroatom bonds formation. However, due to the high bond dissociation energy of unactivated C(sp(2))-F, cross-couplings of mono-fluoroarenes are the most challenging, especially without using transition-metal catalysts. Herein, a photo-induced transition-metal and external photosensitizer free defluorophosphonation of monofluoroarenes via unactivated C(sp(2))-F bond cleavage is reported. Different mono-fluoroarenes have been successfully cross-coupled with dialkyl phosphites in moderate to excellent yields under mild conditions. Mechanistic studies have revealed the possible involvement of a photo-induced SET process and aryl free radical intermediates.
引用
收藏
页码：742 / 746
页数：5
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