- 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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- 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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- Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides
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A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which liberates the desired sulfonyl amidines, generating N2 and CO2 as the only reaction byproducts. Using this simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields. In addition, the reaction can also be directed through a more conventional amidocarbonylation pathway by employing N-monosubstituted amide nucleophiles to afford acyl sulfonyl ureas in good yields.
- Chow, Shiao Y.,Odell, Luke R.
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p. 2515 - 2522
(2017/03/14)
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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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