30765-95-8Relevant articles and documents
Directing-group-assisted markovnikov-selective hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis
Xiao, Qian,Zhang, Hong,Li, Jing-Hong,Jian, Jing-Xin,Tong, Qing-Xiao,Zhong, Jian-Ji
, p. 3604 - 3609 (2021/05/10)
In contrast with the well-developed radical thiol-ene reaction to access anti-Markovnikov-type products, the research on the catalytic Markovnikov-selective hydrothiolation of alkenes is very restricted. Because of the catalyst poisoning of metal catalysts by organosulfur compounds, limited examples of transition-metal-catalyzed thiol-ene reactions have been reported. However, in this work, a directing-group-assisted hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis is found to proceed smoothly to afford Markovnikov-type sulfides with excellent regioselectivity.
Electrochemical-mediated fixation of CO2: three-component synthesis of carbamate compounds from CO2, amines andN-alkenylsulfonamides
Liang, Ying,Pan, Ying-Ming,Tang, Hai-Tao,Xiong, Ting-Kai,Zhang, Min,Zhou, Xue-Qi
, p. 4328 - 4332 (2021/06/30)
An electrocatalyzed three-component cascade reaction of CO2, amines, andN-alkenylsulfonamides is developed, providing an environmentally friendly and efficient method of synthesizing a series of new carbamate compounds. This reaction meets the needs of green chemistry and promotes the participation of carbon dioxide in the three-component reaction by electro-oxidation. Pharmacological activity studies further prove that carbamate compounds have better activity than diamination by-products.
DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
Zhang, Jingran,Li, Xiaoxian,Li, Xuemin,Shi, Haofeng,Sun, Fengxia,Du, Yunfei
, p. 460 - 463 (2021/01/25)
The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.
Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization
Zhao, Quan-Qing,Li, Man,Xue, Xiao-Song,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information, p. 3861 - 3865 (2019/05/24)
A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.
Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis
Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao
, p. 1590 - 1594 (2018/04/30)
A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).
Ruthenium Amide Complexes – Synthesis and Catalytic Activity in Olefin Metathesis and in Ring-Opening Polymerisation
Gawin, Anna,Pump, Eva,Slugovc, Christian,Kajetanowicz, Anna,Grela, Karol
, p. 1766 - 1774 (2018/05/14)
A set of olefin metathesis catalysts bearing a ruthenium amide moiety was synthesised. In the ruthenium amide form these complexes exhibit very low activity in standard metathesis reactions. However, a dramatic increase of activity was observed upon in si
Thiol-ene/oxidation tandem reaction under visible light photocatalysis: Synthesis of alkyl sulfoxides
Guerrero-Corella, Andrea,María Martinez-Gualda, Ana,Ahmadi, Fereshteh,Ming, Enrique,Fraile, Alberto,Alemán, José
supporting information, p. 10463 - 10466 (2017/09/25)
The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (green light). A mechanism has been proposed that is consistent with the experimental results.
Metal-free C-H amination for indole synthesis
Jang, Young Ho,Youn, So Won
, p. 3720 - 3723 (2014/08/05)
An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
Gold-catalyzed cascade cyclization of (azido)ynamides: An efficient strategy for the construction of indoloquinolines
Tokimizu, Yusuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
supporting information, p. 3138 - 3141 (2014/06/23)
(Azido)ynamides were efficiently converted into indoloquinolines by the use of a gold catalyst. While ynamides bearing an allylsilane gave terminal alkenes, ynamides bearing a simple alkene gave cyclopropanes. This reaction proceeds through the formation
Copper-catalyzed oxidative amination and allylic amination of alkenes
Liwosz, Timothy W.,Chemler, Sherry R.
, p. 12771 - 12777 (2013/10/01)
Enamines and enamides are useful synthetic intermediates and common components of bioactive compounds. A new protocol for their direct synthesis by a net alkene C-H amination and allylic amination by using catalytic Cu II in the presence of MnO2 is reported. Reactions between N-aryl sulfonamides and vinyl arenes furnish enamides, allylic amines, indoles, benzothiazine dioxides, and dibenzazepines directly and efficiently. Control experiments further showed that MnO2 alone can promote the reaction in the absence of a copper salt, albeit with lower efficiency. Mechanistic probes support the involvement of nitrogen-radical intermediates. This method is ideal for the synthesis of enamides from 1,1-disubstituted vinyl arenes, which are uncommon substrates in existing oxidative amination protocols. A new protocol for the direct synthesis of enamides and allylic amines by oxidative N-H/C-H coupling of N-sulfonylanilines with vinylarenes is presented. The reaction works in both inter- and intramolecular modes and is catalyzed by copper salts by using MnO2 as the stoichiometric oxidant (see scheme). Nitrogen heterocycles including indoles, benzothiazine dioxides, and dibenzazepines can be formed. Copyright