82757-39-9Relevant articles and documents
Photocatalytic C?H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow
Wen, Zhenghui,Wan, Ting,Vijeta, Arjun,Casadevall, Carla,Buglioni, Laura,Reisner, Erwin,No?l, Timothy
, p. 5265 - 5270 (2021/10/25)
The functionalization of aryl C(sp2)?H bonds is a useful strategy for the late-stage modification of biologically active molecules, especially for the regioselective introduction of azole heterocycles to prepare medicinally-relevant compounds. Herein, we describe a practical photocatalytic transformation using a mesoporous carbon nitride (mpg-CNx) photocatalyst, which enables the efficient azolation of various arenes through direct oxidation. The method exhibits a broad substrate scope and is amenable to the late-stage functionalization of several pharmaceuticals. Due to the heterogeneous nature and high photocatalytic stability of mpg-CNx, the catalyst can be easily recovered and reused leading to greener and more sustainable routes, using either batch or flow processing, to prepare these important compounds of interest in pharmaceutical and agrochemical research.
Oxidation-induced C-H amination leads to a new avenue to build C-N bonds
Yi, Hong,Tang, Zilu,Bian, Changliang,Chen, Hong,Qi, Xiaotian,Yue, Xiaoyu,Lan, Yu,Lee, Jyh-Fu,Lei, Aiwen
supporting information, p. 8984 - 8987 (2017/08/15)
In this work, we develop an oxidation-induced C-H functionalization strategy, which not only leads to a new avenue to build C-N bonds, but also leads to different site-selectivity compared with "classic directing-groups". The high selectivity of our new catalytic system originates from the heterogeneous electron-density distribution of the radical cation species which are induced by single electron transfer between the aromatics and oxidant-Cu(ii) species.
Generation and Rearrangement of 4aH-carbazoles
Kulagowski, Janusz J.,Moody, Christopher J.,Rees, Charles W.
, p. 2725 - 2732 (2007/10/02)
The benzotriazoles (12a-c) bearing ortho-blocked 1-aryl substituents have been decomposed thermally by flash vacuum pyrolysis, and photochemically by irradiation in acetonitrile at 254 nm.The pyrolyses are complex giving mainly mono- and di-methylcarbazoles from (12a), di- and trimethylcarbazoles from (12b), and a tetra- and a penta-methylcarbazole from (12c).All of these products could be formed by generation of 4aH-carbazole intermediates (24) with subsequent thermally-allowed sigmatropic rearrangements (Scheme 6).The photolyses give a different set of products consisting mainly of the cyclopentaquinolines (27a-c) from (12a-c), respectively.These products could be formed from the same 4aH-carbazoles (24) which now undergo photochemical, aza-di-?-methane, rearrangements to give intermediates (29) and hence products (27) (Scheme 7).The 4a-methyl intermediate (29c) is intercepted as the adduct (30) in an extended cycloaddition reaction with acrylonitrile.Key reaction products were synthesized by independent methods.
