137634-62-9Relevant academic research and scientific papers
Rh(III)-Catalyzed Chemoselective C-H Alkenylation and [5 + 1] Annulation with Gem-Difluoromethylene Enabled by the Distinctive Fluorine Effect
Yang, Jian,Shi, Wendi,Chen, Weijie,Gao, Hui,Zhou, Zhi,Yi, Wei
, p. 9711 - 9722 (2021)
The efficient couplings of diverse N-arylureas and gem-difluoromethylene alkynes have been realized via Rh(III)-catalyzed chemoselective C-H alkenylation and [5 + 1] annulation, which were induced by the distinctive fluorine effect to provide the different coordination mode of the Rh(III) catalyst binding to the directing group, thereby giving the direct access to difluorinated 2-alkenyl arylureas and 3,4-dihydroquinazolin-2(1H)-ones bearing both an α-quaternary carbon center and a monofluoroalkenyl moiety with broad substrate compatibility and good functional group tolerance. The synthetic application in C-H alkenylation of the N-pyridylaniline, the late-stage [3 + 2] annulation, and the derivation of the obtained products has been also demonstrated to further strengthen the synthetic utility of the chemodivergent transformations.
Bromide-promoted visible-light-induced reductive minisci reaction with aldehydes
Wang, Zhongzhen,Liu, Qiong,Ji, Xiaochen,Deng, Guo-Jun,Huang, Huawen
, p. 154 - 159 (2020)
Radical addition is a robust tool for bond formation. While ketyl radical reactivity of aldehydes by photoredox has been well-established, herein, we have now revealed a pathway for umpolung addition of aldehydes with or without external reductant. Hence,
Visible-light-mediated photoredox minisci C-H alkylation with alkyl boronic acids using molecular oxygen as an oxidant
Dong, Jianyang,Yue, Fuyang,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 12652 - 12655 (2020/11/02)
Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of heteroarenes with alkyl boronic acids using molecular oxygen as the sole oxidant. This mild protocol uses an inexpensive, green oxidant; permits efficient functionalization of various N-heteroarenes with a broad range of primary and secondary alkyl boronic acids; and is scalable to the gram level. We demonstrated the practicality and sustainability of the protocol by preparing or functionalizing several pharmaceuticals and natural products.
Photoelectrochemical C?H Alkylation of Heteroarenes with Organotrifluoroborates
Yan, Hong,Hou, Zhong-Wei,Xu, Hai-Chao
supporting information, p. 4592 - 4595 (2019/02/13)
A photoelectrochemical method for the C?H alkylation of heteroarenes with organotrifluoroborates has been developed. The merger of electrocatalysis and photoredox catalysis provides a chemical oxidant-free approach for the generation and functionalization
Synthetic method for 2-alkylated4-methylquinoline and derivative thereof
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Paragraph 0046-0051; 0052; 0076, (2019/10/23)
The invention relates generally to a synthetic method for 2-alkylated4-methylquinoline and a derivative thereof. According to the method, under blue LED and iridium catalysis, in a nitrogen atmosphere, the 2-alkylated4-methylquinoline and the derivative t
Visible-Light-Initiated, Photocatalyst-Free Decarboxylative Coupling of Carboxylic Acids with N-Heterocycles
Zhang, Xiao-Yu,Weng, Wei-Zhi,Liang, Hao,Yang, Hua,Zhang, Bo
supporting information, p. 4686 - 4690 (2018/08/09)
A general and efficient protocol for direct C-H alkylation and acylation of N-heterocycles, using readily accessible carboxylic acids as radical precursors under visible-light irradiation without a photocatalyst and an additional acid additive, has been d
Metal-Free-Visible Light C-H Alkylation of Heteroaromatics via Hypervalent Iodine-Promoted Decarboxylation
Genovino, Julien,Lian, Yajing,Zhang, Yuan,Hope, Taylor O.,Juneau, Antoine,Gagné, Yohann,Ingle, Gajendra,Frenette, Mathieu
supporting information, p. 3229 - 3232 (2018/06/11)
A metal-free photoredox C-H alkylation of heteroaromatics from readily available carboxylic acids using an organic photocatalyst and hypervalent iodine reagents under blue LED light is reported. The developed methodology tolerates a broad range of functional groups and can be applied to the late-stage functionalization of drugs and drug-like molecules. The reaction mechanism was investigated with control experiments and photophysical experiments as well as DFT calculations.
A novel iridium/acid co-catalyzed transfer hydrogenative C(sp3)-H bond alkylation to access functionalized N-heteroaromatics
Tan, Zhenda,Jiang, Huanfeng,Zhang, Min
supporting information, p. 9359 - 9362 (2016/07/29)
A novel iridium/acid co-catalysed transfer hydrogenative coupling strategy, enabling direct alkylation of C(sp3)-H bonds and atom-economic access to alkyl chain-lengthened N-heteroaromatics from six-membered 2-alkyl cyclic amines and aldehydes, has been demonstrated. This work has built an important basis to convert cyclic amines, a class of bulk chemical raw materials, into functionalized products.
Tetraaryldisilanes as a novel strategic radical reagent
Yamazaki, Osamu,Togo, Hideo,Malsubayashi, Sou,Yokoyama, Masataka
, p. 3735 - 3747 (2007/10/03)
Reactivity of 1,1,2,2-tetraaryldisilanes as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefins and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilanes showed moderate to good reactivities for these three types of radical reactions. Among some disilanes prepared, 1,1,2,2-tetraphenyldisilane is the most useful in view of its reactivity and ease of preparation.
1,1,2,2-tetraphenyldisilane as a diversified radical reagent
Yamazaki, Osamu,Togo, Hideo,Matsubayashi, Sou,Yokoyama, Masataka
, p. 1921 - 1924 (2007/10/03)
Reactivity of 1,1,2,2-tetraphenyldisilane as a radical reagent in ethanol was studied in reduction of alkyl bromides, addition to olefin and alkylation onto heteroaromatic bases with alkyl bromides. The present organodisilane showed moderate to good reactivities for these three types of radical reactions.
