36458-27-2Relevant academic research and scientific papers
Photoredox-Catalyzed Site-Selective α-C(sp3)?H Alkylation of Primary Amine Derivatives
Ashley, Melissa A.,Yamauchi, Chiaki,Chu, John C. K.,Otsuka, Shinya,Yorimitsu, Hideki,Rovis, Tomislav
supporting information, p. 4002 - 4006 (2019/02/24)
The synthetic utility of tertiary amines to oxidatively generate α-amino radicals is well established, however, primary amines remain challenging because of competitive side reactions. This report describes the site-selective α-functionalization of primary amine derivatives through the generation of α-amino radical intermediates. Employing visible-light photoredox catalysis, primary sulfonamides are coupled with electron-deficient alkenes to efficiently and mildly construct C?C bonds. Interestingly, a divergence between intermolecular hydrogen-atom transfer (HAT) catalysis and intramolecular [1,5] HAT was observed through precise manipulation of the protecting group. This dichotomy was leveraged to achieve excellent α/δ site-selectivity.
Easily accessible auxiliary for palladium-catalyzed intramolecular amination of C(sp2)-H and C(sp3)-H bonds at δ- And ε-Positions
Wang, Chao,Chen, Changpeng,Zhang, Jingyu,Han, Jian,Wang, Qian,Guo, Kun,Liu, Pei,Guan, Mingyu,Yao, Yingming,Zhao, Yingsheng
supporting information, p. 9884 - 9888,5 (2014/10/15)
An easily synthesized and accessible N,O-bidentate auxiliary has been developed for selective C-H activation under palladium catalysis. The novel auxiliary showed its first powerful application in C-H functionalization of remote positions. Both C(sp2)-H and C(sp3)-H bonds at δ- and ε-positions were effectively activated, thus giving tetrahydroquinolines, benzomorpholines, pyrrolidines, and indolines in moderate to excellent yields by palladium-catalyzed intramolecular C-H amination.
Iodination of remote ortho-C-H bonds of arenes via directed S EAr: A streamlined synthesis of tetrahydroquinolines
Nack, William A.,He, Gang,Zhang, Shu-Yu,Lu, Chengxi,Chen, Gong
supporting information, p. 3440 - 3443 (2013/07/26)
A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp3)-H arylation, metal-free ε-C(sp2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.
Pd(II)-catalyzed amination of C-H bonds using single-electron or two-electron oxidants
Mei, Tian-Sheng,Wang, Xisheng,Yu, Jin-Quan
supporting information; experimental part, p. 10806 - 10807 (2009/12/04)
(Chemical Equation Presented) Pd(II)-catalyzed intramolecular amination of arenes is developed using either a one- or two-electron oxidant. The reaction protocol tolerates a wide range of deactivating groups including acetyl, cyano, and nitro groups. This catalytic reaction allows expedient syntheses of broadly useful substituted indolines or indoles.
Instantaneous deprotection of tosylamides and esters with Sml 2/amine/water
Ankner, Tobias,Hilmersson, Goeran
supporting information; experimental part, p. 503 - 506 (2009/07/11)
(Chemical Equation Presented) Sml2/amine/water mediates instantaneous cleavage of tosyl amides and tosyl esters. Highly hindered, sensitive and functionalized substrates were successfully deprotected in near quantitative yield.
Synergistic compositions of carbamate insecticides
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, (2008/06/13)
Carbamate insecticides are potentiated in their control of insects and mites when used in a composition with trifluoromethanesulfonamides.
