A convenient preparation of N-bromosaccharin, source of electrophilic bromine
An extremely straightforward, high yield synthesis of a very reactive electrophilic brominating reagent N-bromosaccharin is described, allowing its preparation in multi-gram quantities and in high purity.
Photochemical regioselective C(sp3)-H amination of amides using N-haloimides
A metal-free regioselective C(sp3)-H amination of amides using N-haloimides in the presence of lithium tert-butoxide and visible light is presented herein. This photoexcited approach is straightforward, and it aminates a wide variety of amides under mild conditions without the use of photocatalysts, external radical initiators, or oxidants. A halogen-bonded intermediate between the tert-butoxide base and the N-haloimide is proposed to be responsible for the increased photoreactivity. Calculations show that the formation of this electron donor-acceptor complex presents an exergonic energy profile.
Pan, Lei,Elmasry, Joseph,Osccorima, Tomas,Cooke, Maria Victoria,Laulhé, Sébastien
supporting information
p. 3389 - 3393
(2021/05/07)
Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols
Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).
The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.
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Paragraph 00113; 00115
(2017/07/28)
Lewis acid-catalyzed electrophilic trifluoromethylthiolation of (Hetero)arenes
(N-Trifluoromethylthio)saccharin has been applied as an electrophilic trifluoromethylthiolating reagent for a broad scope of heteroarenes, electron-donating group (EDG)-activated benzenes, and several electron-rich olefins. Iron(III) and gold(III) catalysts showed complementary activity for different substrates.
Wang, Qiang,Qi, Zisong,Xie, Fang,Li, Xingwei
supporting information
p. 355 - 360
(2015/03/05)
Visible-light promoted catalyst-free imidation of arenes and heteroarenes
We described herein a catalyst-free visible-light photolytic protocol for the imidation of arenes and heteroarenes. N-Bromosaccharin was identified as a viable and chemoselective nitrogen radical precursor that undergoes controllable homolytic cleavage under ambient light irradiation. The reaction can be applied to a number of arenes and heteroarenes with good chemo- and regioselectivity. Mechanistic studies revealed that radical chain termination by electron transfer-proton transfer (ET-PT) is the leading productive pathway for the reaction.
Song, Lu,Zhang, Long,Luo, Sanzhong,Cheng, Jin-Pei
supporting information
p. 14231 - 14234
(2015/01/09)
A peptide bromoiodinane approach for asymmetric bromolactonization
A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology.
Whitehead, Daniel C.,Fhaner, Matthew,Borhan, Babak
supporting information; experimental part
p. 2288 - 2291
(2011/05/16)
Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate
AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.
Kim, Jeum-Jong,Kweon, Deok-Heon,Cho, Su-Dong,Kim, Ho-Kyun,Lee, Sang-Gyeong,Yoon, Yong-Jin
p. 194 - 200
(2007/10/03)
A green preparation of N-chloro- and N-bromosaccharin
The reaction of the sodium salt of saccharin, potassium chloride or bromide and oxone in water at room temperature for 24h produced pure N-chloro- and N-bromosaccharin in 58% and 64% yield, respectively.
De Souza, Soraia P. L.,Da Silva, Joaquim F. M.,De Mattos, Marcio C. S.
p. 935 - 939
(2007/10/03)
Kinetics of Oxidation of Aliphatic Secondary Alcohols by N-Bromosaccharin
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Manoharan, V.,Venkatasubramanian, N.
p. 613 - 615
(2007/10/02)
Kinetic study of the oxidation of D-galactose by N-bromosaccharin in aqueous acetic acid
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Mishra, Usha,Sharma, Kusum,Sharma, Vijay Kumar
p. 155 - 159
(2007/10/02)
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