Selective synthesis of 2-aryl-3-alkenylindoles and 2-aryl-3-alkynylindoles by palladium-catalyzed ligand-promoted annulative coupling of anilines and propargyl alcohols

Li, Qiang; Zhu, Maoshuai; Yan, Xufei; Xia, Ying; Zhou, Xiangge

doi:10.1016/j.jorganchem.2021.121930

Cited by 3 publications

(1 citation statement)

References 38 publications

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“…Therefore, efficient protocols for the synthesis of substituted indoles are highly necessary. Since the development of the classical synthesis of indoles by Fischer, Batcho–Leimgruber, Fukuyama, Nenitzescu, Bartoli, etc., a number of synthetic methods to access indole derivatives have been investigated, − most of which start from 2-ethynylaniline derivatives. − Among these methods, the most frequently used reagents are the strong bases, − such as stoichiometric KH, n -BuLi, t -BuOK, or t -BuONa, and the reported methods mostly used palladium complexes as catalysts. − Although these methods are effective, there are still some disadvantages (Scheme ). (i) Usually, the reported methods require a strong base, , and some cases need a large excessive base (5 equiv), which is not friendly to sensitive functional groups (such as an ester or a carboxyl group).…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of 1,2-Disubstituted Indoles from 2-Ethynylanilines and Benzaldehydes

Wang

Hao

et al. 2022

J. Org. Chem.

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An efficient synthesis of a variety of 1,2-disubstituted indoles from 2-ethynylanilines was developed. Using 2-ethynylanilines and benzaldehydes as starting materials, the target products (1,2-disubstituted indoles) were obtained smoothly through condensation, reduction, and subsequent cyclization. Various functional groups attached to the aryl ring of 1,2-disubstituted indoles were well tolerated. The protocol features easy performance, easily available starting materials, good yield, and a broad substrate scope, showing potential synthetic value for the preparation of a variety of biologically or pharmaceutically active compounds.

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of 1,2-Disubstituted Indoles from 2-Ethynylanilines and Benzaldehydes

Wang

Hao

et al. 2022

J. Org. Chem.

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Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C–H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives

Xiang,

Wang,

et al. 2024

J. Org. Chem.

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Diversity-oriented synthesis strategy for the efficient assembly of indole-fused polycyclic scaffolds via rhodiumcatalyzed NH-indole-directed C−H coupling with propargylic alcohol derivatives in a regioselective manner was developed. Five 2phenyl-1H-indole-embedded core skeletons were synthesized. In particular, three different indole-fused exo-olefin-containing polycycles were realized, which may be manipulated for further chemistry.

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Palladium-Catalyzed Oxidative Annulation Leading to Substituted Pyrrolo[3,2,1-jk]carbazoles by Sequential C–N and C–C Bond Formation

2023

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A novel regioselective annulation of propargylic alcohols with simple carbazoles for the construction of [3,2,1-jk]carbazole scaffolds is described to be the first example of intermolecular synthesis of [3,2,1-jk]carbazoles from simple carbazoles. In situ synthesis of propargyl alcohols from simple, cheap, and easily accessible ketones has also been developed during the one-pot synthesis of [3,2,1-jk]carbazoles.

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Selective synthesis of 2-aryl-3-alkenylindoles and 2-aryl-3-alkynylindoles by palladium-catalyzed ligand-promoted annulative coupling of anilines and propargyl alcohols

Cited by 3 publications

References 38 publications

One-Pot Synthesis of 1,2-Disubstituted Indoles from 2-Ethynylanilines and Benzaldehydes

One-Pot Synthesis of 1,2-Disubstituted Indoles from 2-Ethynylanilines and Benzaldehydes

Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C–H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives

Palladium-Catalyzed Oxidative Annulation Leading to Substituted Pyrrolo[3,2,1-jk]carbazoles by Sequential C–N and C–C Bond Formation

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