We report a conceptually different approach toward E-stilbene syntheses by photoinduced direct C-H arylation of alkenes at rt without the addition of transition metals, with a broad range of aryl halides, including ArI, ArBr, and even ArCl. This is the first time that this reaction has been produced without extra solvent but with 18-crown-6 ether and t-BuOK in only 15 min of reaction.
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http://dx.doi.org/10.1021/jo501474w | DOI Listing |
Org Lett
August 2024
Key Laboratory of Novel Targets and Drug Study for Neural Repair of Zhejiang Province, School of Medicine, Hangzhou City University, 310015 Hangzhou, Zhejiang, China.
Herein, we report a transition-metal-free C-H bond sulfoximidation protocol of sulfonyl hydrazones with hypervalent iodine(III) reagents. A library of novel -sulfaneylidenehydrazonamides was constructed via chemoselective C-N bond formation reactions at aldehyde C-H bonds of sulfonyl hydrazones in the presence of a base. The reaction demonstrated broad substrate group diversity under exceedingly mild reaction conditions, and excellent yields were achieved at room temperature.
View Article and Find Full Text PDFChemSusChem
November 2024
Department of Chemistry and Pharmacy, Chair of Inorganic and General Chemistry and Chair of Inorganic and Organometallic Chemistry, Friedrich Alexander Universität Erlangen - Nürnberg, Egerlandstraße 1, 91058, Erlangen, Germany.
Diphenylformamide 1 and bisformamide 9 are shown to be safe reservoirs and sources of CO. Their perfectly selective decarbonylations are achieved in solution at room temperature with potassium and cesium diarylamide catalysts. 1 is obtained in excellent yields directly from triethylammonium formate, which may be the product of CO scrubbing with NEt and catalytic hydrogenation.
View Article and Find Full Text PDFChemistry
June 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research, Kolkata, Mohanpur, 741246, West Bengal, India.
Catalytic cross-coupling between aryl halides and alkynes is considered an extremely important organic transformation (popularly known as the Sonogashira coupling) and it requires a transition metal-based catalyst. Accomplishing such transformation without any transition metal-based catalyst in the absence of any external stimuli such as heat, photoexcitation or cathodic current is highly challenging. This work reports transition-metal-free cross-coupling between aryl halides and alkynes synthesizing a rich library of internal alkynes without any external stimuli.
View Article and Find Full Text PDFJ Org Chem
April 2024
College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou 425100, Hunan, China.
A simple, efficient, and practical method for the synthesis of S-quinolyl xanthates was developed via TsO-promoted deoxygenative C-H dithiocarbonation of quinoline N-oxides with various potassium O-alkyl xanthates. The reaction performed well under transition-metal-free, base-free, and room-temperature conditions with wide substrate tolerance. Employing potassium --butyl xanthate (BuOCSK) as a nucleophile, some valuable quinoline-2-thiones were unexpectedly obtained in a one-pot reaction without any additional base.
View Article and Find Full Text PDFOrg Biomol Chem
March 2024
College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Hunan, 425100, China.
A convenient, efficient and practical approach for the synthesis of -quinolyl phosphorothioates cheap TsCl promoted deoxygenative C2-H phosphorothiolation of quinoline -oxides with readily available triethylammonium ,-dialkylphosphorothioates was developed. The reaction performed well under transition-metal-free conditions at room temperature with a very short reaction time (10-20 min). Preliminary studies showed that the current transformation underwent a nucleophilic substitution process.
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