- Photocatalytic Oxidative C-H Thiolation: Synthesis of Benzothiazoles and Sulfenylated Indoles
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We report studies on the photocatalytic formation of C-S bonds to form benzothiazoles via an intramolecular cyclization and sulfenylated indoles via an intermolecular reaction. Cyclic voltammetry (CV) and density functional theory studies suggest that benzothiazole formation proceeds via a mechanism that involves an electrophilic sulfur radical, while the indole sulfenylation likely proceeds via a nucleophilic sulfur radical adding into a radical cationic indole. These conditions were successfully extended to several thiobenzamides and indole substrates.
- Aceves, Ernesto Millan,Albright, Samuel T.,Cedano, Mario R.,Dinh, Andrew N.,Gustafson, Jeffrey L.,Nguyen, Ashley D.,Smith, Diane K.
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p. 1648 - 1655
(2019/08/26)
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- Synthesis of: N -alkyl-3-sulfonylindoles and N -alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl- N, N -dialkylanilines
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An efficient and metal-free approach to N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles from 2-alkynyl-N,N-dialkylanilines has been developed. In the presence of iodine and tert-butylhydroperoxide (TBHP), a variety of 2-alkynyl-N,N-dialkylanilines underwent a cascade radical annulation to yield 3-arylsulfonylindoles. In contrast, 3-arylsulfanylindoles were conveniently prepared by iodine mediated electrophilic annulation reactions. The present protocol uses the economical and environmentally friendly I2-TBHP or I2 system, and potentially bioactive N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles with various functional groups were successfully synthesized in moderate to good yields.
- Meesin, Jatuporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Leowanawat, Pawaret,Kuhakarn, Chutima
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p. 3662 - 3669
(2017/07/07)
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- Iron-facilitated iodine-mediated electrophilic annulation of N,N-dimethyl-2-alkynylanilines with disulfides or diselenides
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An efficient synthesis of N-methyl-3-chalcogeno-indoles has been developed via iodine-mediated electrophilic annulation reactions of 2-alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2-alkynylani
- Du, Hui-Ai,Tang, Ri-Yuan,Deng, Chen-Liang,Liu, Yan,Li, Jin-Heng,Zhang, Xing-Guo
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experimental part
p. 2739 - 2748
(2011/12/01)
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- A novel synthetic route to 3-sulfenyland 3-selenylindoles by n-bu 4ni-induced electrophilic cyclization
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3-Sulfenyl-and 3-selenylindoles are prepared in excellent yields by the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization with arylsulfenyl chlorides and arylselenyl chlorides in the presence of a stoichiometric amount of n-Bu4NI.
- Chen, Yu,Cho, Chul-Hee,Larock, Richard C.
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supporting information; experimental part
p. 173 - 176
(2009/06/20)
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- Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu4NI-induced electrophilic cyclization
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(Chemical Equation Presented) 3-Sulfenyl- and 3-selenylindoles are readily synthesized by a two-step process involving the palladium/copper-catalyzed crossing coupling of N,N-dialkyl-ortho-iodoanilines and terminal alkynes and subsequent electrophilic cyclization of the resulting N,N-dialkyl-ortho-(1- alkynyl)anilines with arylsulfenyl chlorides or arylselenyl chlorides. The presence of a stoichiometric amount of n-Bu4NI is crucial to the success of the electrophilic cyclization. A variety of 3-sulfenyl- and 3-selenylindole derivatives bearing alkyl, vinylic, aryl, and heteroaryl substituents have been prepared in good to excellent yields (up to 99%). By employing N,N-dibenzyl-ortho-iodoanilines, a 3-sulfenyl-N-H-indole has been successfully prepared. In addition, 3-sulfonyl- and 3-sulfinylindoles have also been successfully prepared by facile oxidation of the corresponding 3-sulfenylindoles.
- Chen, Yu,Cho, Chul-Hee,Shi, Feng,Larock, Richard C.
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supporting information; experimental part
p. 6802 - 6811
(2009/12/30)
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