期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 63, 页码 14453-14460出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202002868
关键词
C-H activation; EBX-reagents; hydrogen atom transfer; metal-free processes; photochemistry
资金
- Hellenic Foundation for Research and Innovation (HFRI) - 1stCall for H.F.R.I. Research Projects [655]
- State Scholarships Foundation (IKY)
- State Scholarships Foundation (IKY) through the Supporting Post-Doctoral Researchers-Call B [MIS 5033021]
- European Social Fund (ESF)
- COST Action C-H Activation in Organic Synthesis (CHAOS) [CA15106]
- NCCR chemical biology of the Swiss National Science Foundation
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 alpha-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.
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