The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary mechanistic experiments indicate that this tandem process involves two possible mechanistic pathways for the formation of quinazolines via catalytic carbopalladation of the cyano group.
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http://dx.doi.org/10.1021/acs.orglett.8b01070 | DOI Listing |
Org Lett
November 2024
Department of Chemistry, Chonnam National University, Gwangju 61186, Republic of Korea.
A palladium-catalyzed three-component reaction enabled the synthesis of -formylanilines from aryl iodides, NaN, and oxalic acid. This one-pot process involves aminocarbonylation, the Curtius rearrangement, and reduction using oxalic acid as both a carbon monoxide and hydrogen donor. The method has a broad substrate scope, tolerates various functional groups, and delivers -formylanilines in high yields, making it a green and useful synthetic approach.
View Article and Find Full Text PDFOrg Biomol Chem
October 2024
Department of Chemistry, Tunghai University, No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung 407224, Taiwan.
A series of unsymmetrical 2,4-disubstituted pyranocoumarins and 3-bromo-2-(4-bromoalkoxy)-derived pyranocoumarins were synthesized the palladium-catalyzed C-H arylation of 4-phenyl-4,5-pyrano[3,2-]chromen-5-ones with aryl iodide and the three-component reaction of 4-phenyl-4,5-pyrano[3,2-]chromen-5-one with bromine and cyclic ether, respectively.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Frontiers Science Center for Transformative Molecules, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.
Herein, we report a synergistic photoredox/palladium catalytic system for the efficient enantioconvergent synthesis of axially chiral esters from racemic heterobiaryl (pseudo)halides (bromides/triflates) with CO and alkyl bromides under mild conditions. A wide range of axially chiral esters were obtained in good to high yields with excellent enantioselectivities. Detailed mechanistic studies unveiled that the ratio of photocatalyst and palladium catalyst exhibited significant impact on the chemo- and enantioselectivities of the reaction.
View Article and Find Full Text PDFChem Commun (Camb)
August 2024
School of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China.
Herein, a straightforward method for rapid access to all-carbon tertrasubstituted alkenes bearing alkyl, aryl and alkynyl groups is established palladium-catalyzed three-component cross-coupling reaction of internal alkynes, haloalkynes and arylboronic acids. This protocol is characterized by a broad substrate scope and excellent chemo- and regioselectivities. The dual beneficial roles of silver salts in activating haloalkynes and inhibiting bromoalkynylation have been demonstrated by serving as both the Lewis acid and halide scavenger.
View Article and Find Full Text PDFOrg Lett
June 2024
Henan University of Chinese Medicine, Zhengzhou 450046, China.
The hybrid nature of Pd(I)-alkyl radical species has enabled a wide array of radical-based transformations. However, in this transformation, the secondary Pd(I)-alkyl radical species are prone to recombining into Pd(II)-alkyl species to give Heck-type products via β-H loss. Herein, we report a visible-light-induced, three-component Pd-catalyzed 1,2-aminoalkylation of alkenes with readily available alkyl halides and amines to construct C-C and C-N bonds simultaneously.
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