Synthesis of Secondary Trifluoromethylated Alkyl Bromides Using 2-Bromo-3,3,3-trifluoropropene as a Radical Acceptor

Abstract

Herein, the first example using commercially available 2-bromo-3,3,3-trifluoropropene (BTP) as a radical acceptor has been reported. Taking advantage of this strategy, a wide range of secondary trifluoromethylated alkyl bromides were synthesized in good to excellent yields with broad functional group tolerance by using redox-active esters as a radical precursor. The practicality of this protocol was further demonstrated by diverse derivations and direct modification of biologically active molecules.

Synthesis of α-CF3 Amides via Palladium-Catalyzed Carbonylation of 2-Bromo-3,3,3-trifluoropropene

“…2-Bromo-3,3,3-trifluoro-1-propene is environmentally friendly (atmospheric greenhouse effect, GWP = 0; atmospheric ozone depletion value, ODP = 0) and used in many organic syntheses, such as the synthesis of α-(trifluoromethyl)styrenes, 11 trifluoromethylated vinyl boron reagent, 12 ethyl 3,3,3-trifluoropropionate, 13 difluoromethyl-substituted 2,3-dihydrobenzoheteroles, 14 trifluoroacrylic acid, 15 and 3-trifluoromethylpyrazole. 16 Developing methods to efficiently convert the compound into fluorine-containing fine chemicals remains a very meaningful area for future research.…”

Photoinduced Decarboxylative C3–H Alkylation of Quinoxalin-2(1H)-ones

“…However, the catalyst-free synthesis of C3–H substituted quinoxaline-2­(1 H )-one is more desirable from the green chemistry point of view because it is an environmentally benign method. Generally, the visible light-activated electron donor–acceptor (EDA) complex strategy comes under the catalyst-free approach . Very recently, two groups reported photoinduced catalyst-free direct acylation and amination of a series of quinoxalin-2­(1 H )-ones.…”

Synthesis of Secondary Trifluoromethyl Boronic Esters through Visible Light Induced Decarboxylative Alkylation Reactions

“…[5][6] Currently, 18 F-FDG is the most widely applied positron emission tomography (PET) imaging tracer to guide BNCT in clinical; however, it suffers limitations like nonspecificity. [7][8] As a result, 18 F-labeled boramino acids, which take advantages of fluorine and boron synergistically has attracted much attention. For instance, 18 F-trifluoroborate-derived tyrosine ( 18 F-FBY) has demonstrated exciting potential in clinical PET imaging.…”

“…Ga and 177 Lu, the collaboration of 18 F and 10 B also harbours superiorities in tumour radiotheranostics. [3][4] Specifically, when 10 B is bombarded by epithermal neutron, its excited isotope 11 B would produce γ-ray during radioactive decay, this laid the foundation of boron neutron capture therapy (BNCT) for treating locally invasive malignant tumours.…”

“…[3][4] Specifically, when 10 B is bombarded by epithermal neutron, its excited isotope 11 B would produce γ-ray during radioactive decay, this laid the foundation of boron neutron capture therapy (BNCT) for treating locally invasive malignant tumours. [5][6] Currently, 18 F-FDG is the most widely applied positron emission tomography (PET) imaging tracer to guide BNCT in clinical; however, it suffers limitations like nonspecificity. [7][8] As a result, 18 F-labeled boramino acids, which take advantages of fluorine and boron synergistically has attracted much attention.…”