Intermolecular annulation of enynes and propargyl esters to selectively produce styrenes or fluorenes is reported. The divergent arene syntheses involve a Au-catalyzed, two-pot, multistep process proceeding by cis-diastereoselective cyclopropanation, cycloisomerization, and, finally, annulation or elimination.
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http://dx.doi.org/10.1021/ja710990d | DOI Listing |
Acc Chem Res
January 2025
Department of Chemistry and Chemistry Institution for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.
ConspectusControlling selectivity through manipulation of reaction intermediates remains one of the most enduring challenges in organic chemistry, providing novel solutions for selective C-C π-bond functionalization. This approach, guided by activation principles, provides an effective method for selective functional group installation, enabling direct synthesis of organic molecules that are inaccessible through conventional pathways. In particular, the selective functionalization of N-conjugated allenes and alkynes has emerged as a promising research focus, driven by advances in controlling reactive intermediates and activation strategies.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of OSPC, CSIR-Indian Institute of Chemical Technology, Habsiguda, Hyderabad 500007, India.
Annulations through dual C-H activation represent a powerful tool to selectively assemble multi-cyclic scaffolds. We present herein a palladium-catalyzed -/-C-H-annulation of biphenyl amines with 1,6-enynes. This regioselective non-rollover cyclometallation was achieved through meticulous tuning of electronic factors of both the partners.
View Article and Find Full Text PDFOrg Lett
October 2024
State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China.
Org Biomol Chem
September 2024
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
A novel visible-light-driven photoredox-catalyzed cascade bicyclization of 1,7-enynes with aqueous sulfoxonium ylides is reported. The reaction is highly chemoselective with three new C-C bonds, two new rings, and an all-carbon quaternary stereocenter constructed in a one-pot fashion. This mild protocol features a remarkably broad substrate scope with good functional group tolerance, providing a general and practical approach to access various cyclopenta[]quinolines.
View Article and Find Full Text PDFOrg Lett
August 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research Berhampur, Berhampur, Odisha 760010, India.
We report an unprecedented application of skipped enynes as bis-electrophiles under palladium/Brønsted acid catalysis. A [3 + 3] annulation of skipped enynes with 4-hydroxy coumarins as bis-nucleophiles enables a completely atom-economic synthesis of fused O-heterocycles. The reaction is proposed to proceed via the Pd-catalyzed C-H activation of the skipped enyne leading to a diene, which upon subsequent activation by Pd and an O-nucleophilic attack leads to the regioselective formation of a six-membered heterocyclic ring, with a vinyl substituent.
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