- Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
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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.
- Yang, Dong,Shi, Jingqi,Chen, Jiaming,Jia, Xiaoqi,Shi, Cuiying,Ma, Lifang,Li, Ziyuan
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p. 18966 - 18973
(2021/06/03)
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- Sulfonyl formamidine compound as well as synthesis method and application thereof
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The invention discloses a sulfonyl formamidine compound as well as a synthesis method and application thereof, and belongs to the technical field of chemical synthesis and medicines. The structural general formula of the sulfonyl formamidine compound is shown in the description, wherein in the formula, R1 and R2 fragments are cyclic amines or cyclic amines with different substituents, and the substituents are at least one of fluorine, chlorine, bromine, cyano, amino, aryl, hydroxyl, carbonyl, ester group and nitro; and R3 is any one of phenyl and derivatives thereof, naphthyl and derivatives thereof, pyridine and derivatives thereof, and thiophene and derivatives thereof. According to the invention, the sulfonyl formamidine compound is prepared by one-step direct dehydrogenation coupling of simple and easily available N-methyl tertiary amine and sulfonamide through a simple catalytic system, is pollution-free, and can be applied to later derivation of drugs.
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Paragraph 0040-0045
(2021/02/10)
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- Electrochemically generatedN-iodoaminium species as key intermediates for selective methyl sulphonylimination of tertiary amines
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Reported herein is a straightforward protocol for approachingN-sulphonylamidinesviaan electricity-driven, iodine-mediated cross dehydrogenative condensation (CDC) between sulphonamides and tertiary amines, which features exclusive N-CH3selectivity for the amine partners. Mechanistic studies indicate that anin situgeneratedN-iodoaminium species serves as the key intermediate.
- Huang, Binbin,Yang, Chao,Zhou, Jia,Xia, Wujiong
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supporting information
p. 5010 - 5013
(2020/05/18)
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- Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage
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Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.
- Gui, Jiao,Xie, Haisheng,Jiang, Huanfeng,Zeng, Wei
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supporting information
p. 2804 - 2807
(2019/04/30)
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- Air-Induced One-Pot Synthesis of N-Sulfonylformamidines from Sulfonyl Chlorides, NaN3, and Tertiary/Secondary Amines
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An efficient and practical one-pot strategy for the synthesis of N-sulfonylformamidines was developed by directly using easily available sulfonyl chlorides, sodium azide and tertiary/secondary amines in the presence of 5 mol-% CuBr2 under aerob
- Bi, Wen-Zhu,Zhang, Wen-Jie,Li, Zi-Jie,Xia, Xiao-Yi,Chen, Xiao-Lan,Qu, Ling-Bo,Zhao, Yu-Fen
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supporting information
p. 6071 - 6076
(2019/09/09)
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- N -Sulfonyl acetylketenimine as a highly reactive intermediate for the synthesis of N -sulfonyl amidines
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A highly reactive intermediate N-sulfonyl acetylketenimine was generated from a 3-butyn-2-one participating CuAAC/ring-opening method. Its high reactivity due to bearing two EWGs allowed us to offer the first example of a reaction between ketenimine and amide to synthesize N-sulfonyl amidines efficiently.
- Yang, Weiguang,Huang, Dayun,Zeng, Xiaobao,Luo, Dongping,Wang, Xinyan,Hu, Yuefei
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supporting information
p. 8222 - 8225
(2018/07/29)
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- A Novel Synthesis of N -Sulfonylformamidines from N Sulfonyl sulfonamides
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N -Sulfonylformamidines were synthesized from N -sulfonylsulfonamides by reacting with p -toluenesulfonyl chloride (TsCl) and N, N - disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N, N -disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N -sulfonylformamidines were obtained in 60% to quantitative yields.
- Jeong, Yuri,Ban, Jaeyoung,Lim, Minkyung,Rhee, Hakjune
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supporting information
p. 1867 - 1874
(2018/02/26)
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- Synthesis of N-Sulfonylformamidines by tert-butyl Hydroperoxide–Promoted, metal-free, direct oxidative dehydrogenation of aliphatic amines
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A direct and convenient metal-free method to prepare sulfonyl amidines in the presence of aqueous tert-butyl hydroperoxide (T-HYDRO) has been developed. Different tertiary and secondary amines were tested for compatibility with the oxidative conditions and could be coupled with sulfonyl azides to form the corresponding amidines in moderate to good yields.
- Rouzi, Ayijiamali,Hudabaierdi, Ruzeahong,Wusiman, Abudureheman
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p. 2475 - 2481
(2018/04/14)
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- Three-component synthesis of N-sulfonylformamidines in the presence of magnetic cellulose supported N-heterocyclic carbene-copper complex, as an efficient heterogeneous nanocatalyst
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A cellulose based magnetic nanocomposite possessing NHC-Cu Complex has been synthesized and characterized. It was then applied as a highly active catalyst in one-pot three-component reaction of sulfonyl azides, secondary amines and triethylamine to afford
- Shojaei, Salman,Ghasemi, Zarrin,Shahrisa, Aziz
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supporting information
p. 3957 - 3965
(2017/09/26)
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- Interception of amide ylides with sulfonamides: Synthesis of (: E)- N -sulfonyl amidines catalyzed by Zn(OTf)2
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Through the interception of amide ylides with sulfonamides, we herein report the first general example of an intermolecular condensation reaction between sulfonamides and amides. Beyond formamides, this approach was successfully applied to a variety of lactams and linear amides, giving rise to a broad array of (E)-N-sulfonyl amidines.
- Chen, Jijun,Long, Wenhao,Fang, Shangwen,Yang, Yonggang,Wan, Xiaobing
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supporting information
p. 13256 - 13259
(2017/12/26)
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- Improved synthesis of N-sulfonylformamidine derivatives promoted by thionyl chloride
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An improved synthesis of N-sulfonylformamidine derivatives has been developed involving direct condensation of various sulfonamides and formamides in the presence of thionyl chloride using chloroform as solvent. Detailed synthetic studies indicate that th
- Hudabaierdi, Ruzeahong,Wusiman, Abudureheman,Mulati, Ayinigeer
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p. 485 - 489
(2017/05/01)
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- Bromoform reaction of tertiary amines with N,N-dibromosulfonamides or NBS/sulfonamides
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A new bromoform reaction of tertiary amines with N,N-dibromosulfonamides or NBS/sulfonamides has been developed. A series of amidines were prepared with moderate to good yields via a Csp3-Csp3 bond cleavage. This journal is
- Chen, Jie,Guo, Yu-Ping,Sun, Ming-Hui,Fan, Guo-Tao,Zhou, Ling
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supporting information
p. 12367 - 12370
(2014/12/11)
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- Direct condensation of sulfonamide and formamide: NaI-catalyzed synthesis of N-sulfonyl formamidine using TBHP as oxidant
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A new N-sulfonyl formamidine synthesis was developed via NaI-catalyzed direct condensation of sulfonamide and formamide. The green methodology is featured by high atom economy, easily available starting materials, the lack of need for a transition-metal c
- Chen, Shulin,Xu, Yuan,Wan, Xiaobing
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supporting information; experimental part
p. 6152 - 6155
(2012/01/03)
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- CuCI/CCI4-Promoted Convenient Synthesis of Sulfonyl Amidines from Tertiary Amines and Sulfonyl Azides
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Chemical Equation Presentation Promoted by CuCI/CCI4, a variety of sulfonyl azides and tertiary amines were successfully coupled to give sulfonyl amidine derivatives in good to excellent yields. A possible mechanism for this reaction Is discussed
- Xu, Xiaoliang,Ge, Zhichuang,Cheng, Dongping,Lei, Ma.,Lu, Chunshan,Zhang, Qunfeng,Yao, Nan,Li, Xiaonian
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supporting information; experimental part
p. 897 - 899
(2010/06/13)
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- An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide
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It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives. Copyright
- Xu, Xiaoliang,Li, Xiaonian,Ma, Lei,Ye, Ning,Weng, Bojie
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supporting information; experimental part
p. 14048 - 14049
(2009/03/11)
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- TRICHLOROMETHYL GROUP AS A NUCLEOFUGE IN THE REACTION OF AZOMETHINES WITH AMINES
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In the reaction of N-(2,2,2-trichloroethylidene)-4-R-benzoylsulfonamides (R = H, Cl, CH3) with aliphatic secondary amines N,N-dialkyl-N'-arylsulfonylformamidines are formed as substitution products of the trichloromethyl group.Thus, the trichloromethyl gr
- Krasnov, V.L.,Vasyanina, G.I.,Bodrikov, I.V.
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p. 1359 - 1362
(2007/10/02)
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- Thermolysis and Photolysis of Some 5-Amino-4-methoxycarbonyl-Δ2-1,2,3-triazolines
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Thermolysis of 5-amino-4-methyl-4-methoxycarbonyl-Δ2-1,2,3-triazolines leads to amidines and 1-methoxycarbonyl diazoethane.If the N1 substituent is a tosyl or benzoyl group, the corresponding triazoline is not isolated, the azide addition to the olefin gives directly the thermolysis products at room temperature.Triazoline photolysis leads to amino aziridines which are azomethine ylids.
- Bourgois, J.,Mathieu, A.,Texier, F.
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p. 513 - 515
(2007/10/02)
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