- A convenient and general method for the synthesis of indole-2,3- dicarboxylates and 2-arylindole-3-carboxylates
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A transition-metal-free, simple and efficient one-pot method for the synthesis of indole-2,3-dicarboxylates and 2-aryl-indole-3-carboxylates is described. The corresponding products are obtained by a domino hydroamination/Fischer indole cyclization in goo
- Sayyed, Iliyas Ali,Alex, Karolin,Tillack, Annegret,Schwarz, Nicolle,Michalik, Dirk,Beller, Matthias
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- Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles
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Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is
- Zhang, Lei,Chen, Junyu,Chen, Xiahe,Zheng, Xiangyun,Zhou, Jian,Zhong, Tianshuo,Chen, Zhiwei,Yang, Yun-Fang,Jiang, Xinpeng,She, Yuan-Bin,Yu, Chuanming
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p. 7415 - 7418
(2020/07/15)
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- Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
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Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.
- Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro
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p. 734 - 745
(2016/01/15)
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- C-H Activation-Based Traceless Synthesis via Electrophilic Removal of a Directing Group. Rhodium(III)-Catalyzed Entry into Indoles from N-Nitroso and α-Diazo-β-keto Compounds
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A distinct C-H activation-based traceless synthetic protocol via electrophilic removal of a directing group is reported, complementing the currently exclusively used nucleophilic strategy. Rh(III)-catalyzed, N-nitroso-directed C-H activation allows the development of a traceless, atom- and step-economic, cascade approach for the synthesis of indole skeletons, starting from readily available N-nitroso and α-diazo-β-keto compounds. Importantly, the cyclization/denitrosation reaction represents a hitherto unobserved reactivity pattern for the N-nitroso group.
- Wang, Jie,Wang, Mingyang,Chen, Kehao,Zha, Shanke,Song, Chao,Zhu, Jin
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p. 1178 - 1181
(2016/03/15)
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