- Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes
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A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.
- He, Xinxu,He, Yanyang,Qin, Xiaowen,Wu, Xiao-Feng,Yin, Zhiping
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supporting information
p. 5831 - 5834
(2021/11/17)
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- Rhodium(iii)-catalyzed allylic C-H bond amination. Synthesis of cyclic amines from ω-unsaturated N-sulfonylamines
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For the first time, intramolecular allylic amination was conducted using rhodium(iii) according to an "inner-sphere" type mechanism with amines activated by only one electron-withdrawing group. The activation of C(sp 3)-H bonds was chemoselective and allows the access to a variety of substituted cyclic amines such as pyrrolidines and piperidines.
- Cochet, Thomas,Bellosta, Veronique,Roche, Didier,Ortholand, Jean-Yves,Greiner, Alfred,Cossy, Janine
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supporting information
p. 10745 - 10747
(2013/01/15)
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- Enantioselective synthesis of pyrrolidine-, Piperidine-, and azepane-type N -heterocycles with α-alkenyl substitution: The CpRu-catalyzed dehydrative intramolecular N -allylation approach
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A cationic CpRu complex of chiral picolinic acid derivatives [(R)- or (S)-Cl-Naph-PyCOOCH2CH=CH2] catalyzes asymmetric intramolecular dehydrative N-allylation of N-substituted ω-amino- and -aminocarbonyl allylic alcohols with a substrate/catalyst ratio of up to 2000 to give α-alkenyl pyrrolidine-, piperidine-, and azepane-type N-heterocycles with an enantiomer ratio of up to >99:1. The wide range of applicable N-substitutions, including Boc, Cbz, Ac, Bz, acryloyl, crotonoyl, formyl, and Ts, significantly facilitates further manipulation toward natural product synthesis.
- Seki, Tomoaki,Tanaka, Shinji,Kitamura, Masato
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supporting information; experimental part
p. 608 - 611
(2012/03/10)
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