A new gold(I) self-relay catalysis reaction enabling the annulative oxygenation of propargylic alcohols with various O-nucleophiles, such as carboxylic acids, alcohols and TBHP, is reported, producing a series of functionalized benzofurans in moderate to good yields under mild conditions. This protocol benefits from the π- and σ-Lewis acid capability of gold complexes, demonstrating high molecular convergence, broad substrate flexibility, high functional group compatibility and mild conditions.
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http://dx.doi.org/10.1039/d3cc00089c | DOI Listing |
J Org Chem
November 2024
Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi dell'Aquila, Via Vetoio, 67100 Coppito, AQ, Italy.
The distinctive features of gold self-relay catalysts were alternatively utilized in the intriguing cascade condensation of 2-aminobenzaldehydes with alcohols and amines. Using NaAuCl·2HO as a catalyst, a range of 13-alkyloxy-7,11-dihydro-6,13-6,12-[1,2]benzenoquinazolino[3,4-]quinazoline derivatives was produced in good to high yields through AB condensation of various 2-aminobenzaldehydes with alcohols. By carefully choosing the reaction conditions, gold catalysis also proved effective for AB condensation with primary aryl- and benzylamines, facilitating the synthesis of challenging McGeachin bisaminals, including a chiral nonracemic derivative of 2-()-methylbenzylamine.
View Article and Find Full Text PDFJ Org Chem
November 2024
School of Chemistry & Materials Science and Analyzing and Test Center, Jiangsu Normal University, Xuzhou 221116, China.
A gold self-relay catalysis driving a double annulation cascade starting from soft electron-biased 1,2-di(-aminoaryl)alkynes and aldehydes is reported, enabling regioselective access to produce a series of [5]azahelicenes depending on the substitution pattern in generally good yields under mild conditions. This protocol exploits and unifies the π- and σ-Lewis acid capability of gold catalysts, featuring high molecular convergence, broad substrate flexibility, and good functional group compatibility and regioselectivity.
View Article and Find Full Text PDFJ Am Chem Soc
February 2024
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China.
Dicarboxylic acids and derivatives are important building blocks in organic synthesis, biochemistry, and the polymer industry. Although catalytic dicarboxylation with CO represents a straightforward and sustainable route to dicarboxylic acids, it is still highly challenging and limited to generation of achiral or racemic dicarboxylic acids. To date, catalytic asymmetric dicarboxylation with CO to give chiral dicarboxylic acids has not been reported.
View Article and Find Full Text PDFChem Commun (Camb)
March 2023
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China.
A new gold(I) self-relay catalysis reaction enabling the annulative oxygenation of propargylic alcohols with various O-nucleophiles, such as carboxylic acids, alcohols and TBHP, is reported, producing a series of functionalized benzofurans in moderate to good yields under mild conditions. This protocol benefits from the π- and σ-Lewis acid capability of gold complexes, demonstrating high molecular convergence, broad substrate flexibility, high functional group compatibility and mild conditions.
View Article and Find Full Text PDFOrg Lett
March 2016
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
A self-relay rhodium(I)-catalyzed cyclization of alkyne-azides with two σ-donor/π-acceptor ligands (isonitriles and CO) to form sequentially multiple-fused heterocycle systems via tandem nitrene transformation and aza-Pauson-Khand cyclization has been developed. In this approach, an intriguing chemoselective insertion process of isonitriles superior to CO was observed. This reaction provides an alternative strategy to synthesize functionalized pyrrolo[2,3-b]indole scaffolds.
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