15787-48-1Relevant articles and documents
Cross-Dehydrogenative Coupling of Strong C(sp3)-H with N-Heteroarenes through Visible-Light-Induced Energy Transfer
An, Guanghui,Li, Guangming,Tian, Chao,Tian, Haitao,Yang, Hui
supporting information, p. 7709 - 7715 (2020/10/09)
The sustainable cross-dehydrogenative coupling of strong C(sp3)-H with N-heteroarenes has been developed using an efficient organic photocatalyst. It features atomic- and step-economy, and acid-free conditions. Mechanism studies suggest a previous elusive
Visible-Light-Mediated C-H Alkylation of Pyridine Derivatives
Rammal, Fatima,Gao, Di,Boujnah, Sondes,Gaumont, Annie-Claude,Hussein, Aqeel A.,Lakhdar, Sami
, p. 7671 - 7675 (2020/10/09)
We report herein a visible-light-mediated C-H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this process a useful synthetic platform for the construction of structurally strained heterocycles. Detailed mechanistic investigations, including density functional theory calculations and quantum yield measurement, allowed us to understand factors controlling the reactivity and the selectivity of the reaction.
Organocatalyzed, Visible-Light Photoredox-Mediated, One-Pot Minisci Reaction Using Carboxylic Acids via N-(Acyloxy)phthalimides
Sherwood, Trevor C.,Li, Ning,Yazdani, Aliza N.,Dhar, T. G. Murali
, p. 3000 - 3012 (2018/03/09)
An improved, one-pot Minisci reaction has been developed using visible light, an organic photocatalyst, and carboxylic acids as radical precursors via the intermediacy of in situ-generated N-(acyloxy)phthalimides. The conditions employed are mild, demonstrate a high degree of functional group tolerance, and do not require a large excess of the carboxylic acid reactant. As a result, this reaction can be applied to drug-like scaffolds and molecules with sensitive functional groups, enabling late-stage functionalization, which is of high interest to medicinal chemistry.
Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles
Tang, Ren-Jin,Kang, Lei,Yang, Luo
supporting information, p. 2055 - 2060 (2015/06/23)
A metal-free oxidative decarbonylative coupling of aliphatic aldehydes with various electron-deficient heterocycles has been developed. This reaction is supposed to be realized via a Minisci-type mechanism, based on the substrate scope, regioselectivity and radical trapping experiments. The ready availability of aliphatic aldehydes, metal-free conditions and broad substrate scope should make this method attractive for the late-stage alkylation of bioactive heterocycles.
Benzoyl peroxide promoted radical ortho-alkylation of nitrogen heteroaromatics with simple alkanes and alcohols
Fang, Lei,Chen, Liangshun,Yu, Jianjun,Wang, Limin
, p. 1910 - 1914 (2015/03/18)
A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols leads to the corresponding 2-alkylpyridines with high regioselectivity in moderate to good yields without an additional reduction step to remove the activated group. A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols has been developed. The strategy allowed convenient access to various 2-alkylpyridines in moderate to good yields without an additional reduction step to remove the activated group.
Radical Decarboxylative Alkylation onto Heteroaromatic Bases with Trivalent Iodine Compounds
Togo, Hideo,Aoki, Masahiko,Kuramochi, Tadashi,Yokoyama, Masataka
, p. 2417 - 2428 (2007/10/02)
Heteroaromatic bases containing nitrogen atoms were easily alkylated with carboxylic acids in the presence of benzene and pentafluorobenzene via radical pathways.Similarly, the alkylation onto heteroaromatic bases was carried out with oxalic acid monoalkyl esters, which were prepared from alcohols and oxalyl dichloride, in the presence of the same trivalent iodine compounds.Moreover, this system was applied to the synthesis of C-nucleosides with the carboxylic acids bearing a sugar moiety.
