95193-00-3Relevant academic research and scientific papers
A Metal–Organic Framework as a Multiphoton Excitation Regulator for the Activation of Inert C(sp3)?H Bonds and Oxygen
Cai, Junkai,Cai, Wei,Du, Zenggang,Duan, Chunying,He, Cheng,Ji, Guanfeng,Wei, Jianwei,Zhao, Liang
supporting information, (2021/11/27)
The activation and oxidization of inert C(sp3)?H bonds into value-added chemicals affords attractively economic and ecological benefits as well as central challenge in modern chemistry. Inspired by the natural enzymatic transformation, herein,
Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
Shabalin, Dmitrii A.,Dvorko, Marina Yu.,Schmidt, Elena Yu.,Trofimov, Boris A.
supporting information, p. 2703 - 2715 (2021/04/07)
A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.
Time-Resolved EPR Revealed the Formation, Structure, and Reactivity of N -Centered Radicals in an Electrochemical C(sp3)-H Arylation Reaction
Alhumade, Hesham,Gao, Renfei,Huang, Cunlong,Lei, Aiwen,Liu, Yichang,Liu, Zhao,Qi, Xiaotian,Shi, Biyin,Wang, Shengchun
supporting information, p. 20863 - 20872 (2021/12/14)
Electrochemical synthesis has been rapidly developed over the past few years, while a vast majority of the reactions proceed through a radical pathway. Understanding the properties of radical intermediates is crucial in the mechanistic study of electroche
Scalable Photoelectrochemical Dehydrogenative Cross-Coupling of Heteroarenes with Aliphatic C?H Bonds
Chen, Peng-Yu,Xu, Hai-Chao,Xu, Pin
supporting information, p. 14275 - 14280 (2020/07/13)
Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C?H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross-coupling of heteroarenes and C(sp3)?H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3)?H donor is converted to a nucleophilic carbon radical through H-atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl?. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products.
Visible Light-Promoted Aliphatic C-H Arylation Using Selectfluor as a Hydrogen Atom Transfer Reagent
Zhao, Hong,Jin, Jian
supporting information, p. 6179 - 6184 (2019/09/06)
A mild, practical method for direct arylation of unactivated C(sp3)-H bonds with heteroarenes has been achieved via photochemistry. Selectfluor is used as a hydrogen atom transfer reagent under visible light irradiation. A diverse range of chem
Acid-catalyzed tandem reaction for the synthesis of pyridine derivatives via C=C/C(sp3)-N bond cleavage of enones and primary amines
Mao, Zhong-Yuan,Liao, Xiao-Yun,Wang, Heng-Shan,Wang, Chun-Gu,Huang, Ke-Bin,Pan, Ying-Ming
, p. 13123 - 13129 (2017/03/11)
A one-pot acid-catalyzed tandem reaction has been developed without any metallic reagents or extra oxidants. This reaction involves a C=C bond cleavage of enones via a “masked” reverse Aldol reaction, and C(sp3)-N bond cleavage of primary amines to provide nitrogen sources for the assembly of pyridine derivatives in high yields with excellent functional group tolerance.
Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis
McCallum,Barriault
, p. 4754 - 4758 (2016/07/06)
Although visible light photoredox catalysis has emerged as a powerful tool for the construction of C-C bonds, common catalysts and/or their photoexcited states suffer from low redox potentials, limiting their applicability to alkyl radical generation from substrates with activated carbon-halogen bonds. Radicals derived from these activated compounds, being highly electrophilic or stabilized, do not undergo efficient addition to heteroarenes. Herein we describe the photocatalytic generation of nucleophilic alkyl radicals from unactivated bromoalkanes as part of a universal and efficient cross-coupling strategy for the direct alkylation of heteroarenes using a dimeric gold(i) photoredox catalyst, [Au2(bis(diphenylphosphino)methane)2]Cl2. The method proves to be efficient for alkylation of arenes under mild conditions in the absence of directing groups.
