1599458-29-3Relevant academic research and scientific papers
Visible Light-Induced Direct S0→ TnTransition of Benzophenone Promotes C(sp3)-H Alkynylation of Ethers and Amides
Matsumoto, Koki,Nakajima, Masaya,Nemoto, Tetsuhiro
, p. 11802 - 11811 (2020/10/23)
Benzophenone has an S0 → S1 absorption band at 365 nm. However, the rarely reported S0 → Tn transition occurs upon irradiation at longer wavelengths. Herein, we employed benzophenone as a catalyst and exploited its S0 → Tn transition in C(sp3)-H alkynylations with hypervalent iodine reagents. The selective benzophenone excitation prevented alkynylating reagent decomposition, enabling the reaction to proceed under mild conditions. The reaction mechanism was investigated by spectroscopic and computational studies.
Visible-Light-Induced Alkynylation of α-C–H Bonds of Ethers with Alkynyl Bromides without External Photocatalyst
Xie, Xiaofei,Liu, Jie,Wang, Lei,Wang, Min
, p. 1534 - 1538 (2019/09/06)
A direct alkynylation of C(sp3)–H bonds adjacent to an oxygen atom of ethers under visible light irradiation was developed in the absence of an external photocatalyst. The reaction of ethers and alkynyl bromides underwent smoothly to generate the corresponding products in good yields with excellent functional-group tolerance. Initial mechanistic experimental results indicated that the reaction may involve a free radical pathway.
Method for synthesizing alpha-alkynyl substituted ether compounds
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Paragraph 0037-0039, (2018/04/01)
The invention discloses a method for preparing alpha-alkynyl substituted ether compounds. The method comprises the following steps: taking propiolic acid as a raw material, and synthesizing substituted phenylpropiolic acid under conditions of substituted iodobenzene, 1,8-diazabicyclo[5.4.0]undec-7-ene, (beta-4)-platinu and dimethyl sulfoxide; taking substituted phenylpropiolic acid and p-bromophenol as raw materials, and synthesizing p-bromophenyl substituted phenylpropiolic acid ester under the conditions of 4-dimethylaminopyridine and N,N'-Dicyclohexylcarbodiimide; and performing an alkynylation reaction on the p-bromophenyl substituted phenylpropiolic acid ester in participation of tert-butyl hydroperoxide, cesium carbonate and tetrahydrofuran, and finally synthesizing alpha-alkynyl substituted ether products. According to the method disclosed by the invention, simple and readily available acetylene esters serve as an alkynylation reagent, and the target products, namely alpha-alkynyl substituted ether compounds, are synthesized in a green and environmental-friendly manner under mild conditions. The compounds play an important role in construction of multiple medical intermediates and bio-active structures.
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
Practical and highly selective C-H functionalization of structurally diverse ethers
Wan, Miao,Meng, Zhilin,Lou, Hongxiang,Liu, Lei
supporting information, p. 13845 - 13849 (2015/01/16)
A trityl ion mediated C-H functionalization of ethers with a wide range of nucleophiles at ambient temperature has been developed. The reaction displays high chemo-selectivity and good functional group tolerance. The protocol also exhibits excellent regio- and diastereoselectivities for the unsymmetric ethers, thus stereoselectively generating highly functionalized disubstituted 2,5-trans tetrahydrofurans (THF), 2,6-trans tetrahydropyrans (THP), 2,6-trans dihydropyrans (DHP), and 1,3-trans isochromans, and highlighting the capacity of the protocol in complex molecule synthesis.
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.
