Silver-catalyzed tandem cyclization-elimination reactions of conjugated ene-yne-ketones in PhI(OAc)/triethylamine system lead to the formation of 2-alkenylfurans. 2-Furylsilver carbene and phenyliodonium ylide are proposed as the key intermediates in these transformations.
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http://dx.doi.org/10.1021/acs.orglett.9b00712 | DOI Listing |
J Org Chem
May 2024
School of Chemistry and Chemical Engineering, Guangdong Provincial Key Laboratory of Advanced Drug Delivery, Guangdong Provincial Engineering Center of Topical Precise Drug Delivery System, Guangdong Pharmaceutical University, Guangzhou 510006, PR China.
In this study, we outline a general method for the construction of various (furyl)methyl disulfides from acetyl-masked disulfide nucleophiles and ene-yne-ketones. This protocol is feathered by metal-free, simple experimental conditions, high efficiency, and scalable potential, which make it attractive and practical.
View Article and Find Full Text PDFJ Org Chem
June 2022
School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458, P.R. China.
An efficient and metal-free approach to the construction of diverse functionalized furan derivatives has been developed from ene-yne-ketones and 1,3,5-triazinanes. As an atom-economical and environment-friendly protocol, the new conditions are suitable for selective C-N and C-O bond formation of a wide range of polysubstituted furans in one pot.
View Article and Find Full Text PDFJ Org Chem
May 2019
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China) and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University, Changsha 410081 , China.
Pd(PPh)Cl-catalyzed selective tandem cyclization/oxidation of available conjugated diazo ene-yne-ketones under O atmosphere led to the formation of diazo trisubstituted furans. The Rh(OAc)-mediated selective C(sp)-H insertion at the ortho-position of 2-aryl group (R) of the furan moiety under N atmosphere occurred to construct naphthalene cycle, affording trifunctionalized naphtho[1,2- b]furans. C(sp)-H insertion at the 4-position of the furan ring, and Wolf rearrangement of diazo moiety have not been observed.
View Article and Find Full Text PDFOrg Lett
April 2019
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China) and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University, Changsha 410081 , China.
Silver-catalyzed tandem cyclization-elimination reactions of conjugated ene-yne-ketones in PhI(OAc)/triethylamine system lead to the formation of 2-alkenylfurans. 2-Furylsilver carbene and phenyliodonium ylide are proposed as the key intermediates in these transformations.
View Article and Find Full Text PDFOrg Lett
February 2018
College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science, Shandong Normal University, Jinan 250014, China.
A new anion relay enabled [3 + 3]-annulation of active methylene isocyanides and conjugated ene-yne-ketones was developed for the efficient and straightforward synthesis of biologically valuable furo[3,2-c]pyridine derivatives. In this transformation, a sequential through-bond and through-space anion relay chemistry cascade is involved, which is initiated by an intermolecular Michael addition. Three new bonds and two rings are sequentially constructed from readily available acyclic precursors.
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