1599458-39-5Relevant academic research and scientific papers
Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation
Capaldo, Luca,Ravelli, Davide
, p. 2243 - 2247 (2021/04/05)
A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l
Photochemical Functionalization of Heterocycles with EBX Reagents: C?H Alkynylation versus Deconstructive Ring Cleavage**
Voutyritsa, Errika,Garreau, Marion,Kokotou, Maroula G.,Triandafillidi, Ierasia,Waser, Jér?me,Kokotos, Christoforos G.
supporting information, p. 14453 - 14460 (2020/10/12)
The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C?H functionalization of saturated O-heterocycles, as well as the deconstructive ring-cleavage of S-heterocycles, employing hypervalent iodine alkynylation reagents (ethynylbenziodoxolones, EBX). This photochemical alkynylation is performed utilizing phenylglyoxylic acid as the photoinitiator, leading to the corresponding products in good to high yields, under household fluorescent light bulb irradiation. When O-heterocycles were employed, the expected α-C?H alkynylation took place. In contrast, oxidative ring-opening to form a thioalkyne and an aldehyde was observed with S-heterocycles. Preliminary mechanistic experiments are presented to give first insights into this puzzling divergent reactivity.
Metal-free alkynylation of α-C-H bonds of ethers with ethynylbenziodoxolones
Zhang, Ruo-Yi,Xi, Long-Yi,Zhang, Lei,Liang, Shuai,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 54349 - 54353 (2015/02/02)
A metal-free direct alkylation of C-H bonds adjacent to an oxygen or nitrogen atom was developed. This reaction occurred between saturated heterocycles and ethynylbenziodoxolones under mild conditions. A series of 2-alkynyl cyclic alkanes that contain oxygen or nitrogen atoms were prepared in moderate to good yields. This journal is
KOAc-promoted alkynylation of α-C-H bonds of ethers with alkynyl bromides under transition-metal-free conditions
Zhang, Jiajun,Li, Pinhua,Wang, Lei
, p. 2969 - 2978 (2014/05/06)
A novel KOAc-promoted α-position C-H activation and alkynylation of ethers with alkynyl bromides to 2-alkynyl ethers has been developed under transition-metal-free and simple reaction conditions. In addition, this methodology can also be extended to the vinylation of ethers with vinyl bromides in excellent regio- and stereo-selectivity. A wide range of direct C(sp)-C(sp3) and C(sp2)-C(sp3) bonds has been formed through this protocol, which offers a new and alternative route. This journal is the Partner Organisations 2014.
