Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis

Published on May 24, 2021in RSC Advances3.119
· DOI :10.1039/D0RA10517A
Dong Yang1
Estimated H-index: 1
(Sichuan University),
Jingqi Shi (Sichuan University)+ 4 AuthorsZiyuan Li11
Estimated H-index: 11
(Sichuan University)
Employing sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp3)–C(sp3) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst and oxygen. An alternative mechanism to the previous aerobic photoredox pathway has also been proposed.
#1Renata G. Almeida (UFMG: Universidade Federal de Minas Gerais)H-Index: 4
#2Wagner O. Valença (UFMG: Universidade Federal de Minas Gerais)H-Index: 10
Last. Eufrânio N. da Silva Júnior (UFMG: Universidade Federal de Minas Gerais)H-Index: 28
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Ortho-Quinones represent a special class of redox active compounds associated with a spectrum of pronounced biological activities, including selective cytotoxicity and antimicrobial actions. The modification of the quinone ring by simple nitrogen and sulphur substitutions leads to several new classes of compounds with their own, distinct redox behaviour and equally distinct activities against cancer cell lines and Trypanosoma cruzi. Some of the compounds investigated show activity against T. cru...
#1Jhonnathan BrawleyH-Index: 1
#2Emily EtterH-Index: 1
Last. Christine R. Cremo (University of Nevada, Reno School of Medicine)H-Index: 17
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Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-...
#1Babak Kaboudin (IASBS: Institute for Advanced Studies in Basic Sciences)H-Index: 28
#1Babak Kaboudin (IASBS: Institute for Advanced Studies in Basic Sciences)H-Index: 13
Last. Hiroshi Aoyama (Tokyo University of Pharmacy and Life Sciences)H-Index: 9
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In this report, a green synthesis of N-sulfonyl amidines via the direct reaction of tertiary or secondary amines with sulfonyl azides is described. Transition metal- and catalyst-free conditions were used for the synthesis of biologically important N-sulfonyl amidines. Further studies showed that the reaction proceeded via in situ aerobic oxidation of amines under reflux conditions.
1 CitationsSource
#1Binbin Huang (HIT: Harbin Institute of Technology)H-Index: 11
#2Chao Yang (HIT: Harbin Institute of Technology)H-Index: 20
Last. Wujiong Xia (HIT: Harbin Institute of Technology)H-Index: 21
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Reported herein is a straightforward protocol for approaching N-sulphonylamidines via an electricity-driven, iodine-mediated Cross Dehydrogenative Condensation (CDC) between sulphonamides and tertiary amines, which features exclusive N-CH3 selectivity for the amine partners. Mechanistic studies indicate that an in situ generated N-iodoaminium species serves as the key intermediate.
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#2Zhen Wang (CAS: Chinese Academy of Sciences)H-Index: 109
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Speckle-type POZ protein (SPOP) is overexpressed in the nucleus and misallocated in the cytoplasm in almost all the clear-cell renal cell carcinomas (ccRCC), which leads to kidney tumorigenesis. Pr...
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#1Damián Padín (University of Santiago de Compostela)H-Index: 2
#2Jesús A. Varela (University of Santiago de Compostela)H-Index: 33
Last. Carlos Saá (University of Santiago de Compostela)H-Index: 33
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The Cp*RuCl-based catalyst enables expedient access to a variety of benzofused six-membered azaheterocycles from unprotected o-alkynylanilines and trimethylsilyldiazomethane through an unprecedent ...
1 CitationsSource
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#2Liu ZiningH-Index: 3
Last. Qin Jun (Yunnan University)H-Index: 3
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Herein we describe an efficient copper-catalyzed coupling of sulfonamides with alkylamines to synthesize (E)-N-sulfonylformamidines. The reaction is accomplished under mild conditions without use of corrosive acid or base as additive. It tolerates a broad scope of substrates and generates the products with exclusive (E)-stereoselectivity.
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#1Xixi Zheng (Jiangxi Normal University)H-Index: 1
#2Jie‐Ping Wan (Jiangxi Normal University)H-Index: 1
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#1Wen‐Zhu Bi (Henan University)H-Index: 1
#2Wen-Jie Zhang (Henan University)H-Index: 2
Last. Yufen Zhao (Zhengzhou University)H-Index: 74
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#1Rui Ding (GXNU: Guangxi Normal University)H-Index: 3
#2Hui Chen (GLMU: Guilin Medical University)H-Index: 3
Last. Ying-Ming Pan (GXNU: Guangxi Normal University)H-Index: 28
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