Visible-Light-Promoted C(sp³)-C(sp³) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination

Tan, Kui1,2; He, Jiaan3; Mu, Zhilin3; Ammar, Ibrahim M.2; Che, Chao4,5; Geng, Jin2; Xing, Qi2

2023-11-22

10.1021/acs.orglett.3c03675

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

A photoredox-catalyzed approach for the difluoroalkylation of amino acids was achieved through simultaneous decarboxylation and defluorination processes. This innovative protocol employs commonly available amino acids and trifluoroacetophenones as the primary starting materials, eliminating the necessity for preactivation. This strategy has enabled the synthesis of several difluoroketone functionalized amines in moderate to impressive yields. These synthesized compounds are presented as foundational molecules for subsequent modification. The underlying mechanism for the transformation is anchored in a single electron transfer (SET) radical pathway.

SCI

英语

NI论文

第一

National Natural Science Foundation of China["21977008","22071263"] ; Natural Science Foundation of China[2018A0303130052] ; Natural Science Foundation of Guangdong Province[2019QN01Y127] ; Guangdong Province Zhujiang Talents Program[JCYJ20200109110215774]

Chemistry

Chemistry, Organic

WOS:001121900300001

AMER CHEMICAL SOC

CHEMISTRY

2-s2.0-85179603320

Web of Science

1.Southern Univ Sci & Technol, Shenzhen 518055, Peoples R China
2.Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518059, Peoples R China
3.PolyAdvant, Shenzhen 518000, Peoples R China
4.Peking Univ, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
5.Peking Univ, Key Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

Tan, Kui,He, Jiaan,Mu, Zhilin,et al. Visible-Light-Promoted C(sp³)-C(sp³) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination[J]. ORGANIC LETTERS,2023,25(48):8733-8738.

Tan, Kui.,He, Jiaan.,Mu, Zhilin.,Ammar, Ibrahim M..,Che, Chao.,...&Xing, Qi.(2023).Visible-Light-Promoted C(sp³)-C(sp³) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination.ORGANIC LETTERS,25(48),8733-8738.

Tan, Kui,et al."Visible-Light-Promoted C(sp³)-C(sp³) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination".ORGANIC LETTERS 25.48(2023):8733-8738.