Rhodium(III)‐Catalyzed Cascade C−H Coupling/C‐Terminus Michael Addition of <i>N</i>‐Phenoxy Amides with 1,6‐Enynes

Wei, Yinhui; Jiang, Xinlin; Gao, Hui; Bian, Mengyao; Huang, Yugang; Zhou, Zhi; Yi, Wei

doi:10.1002/slct.202102186

Cited by 5 publications

(3 citation statements)

References 95 publications

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“…[69] A In the same year, the Huang, Zhou, and Yi group reported a Rh-catalyzed reaction employing available 1,6-enynes as substrates through a cascade CÀ H activation/Michael addition sequences, which accomplished a series of polycyclic skeletons in moderate to good yields (Scheme 89). [70] It is noteworthy that a broad variety of functional groups were compatible the catalytic system, and the anticipated products were afforded with opportunities for dual CÀ H functionalization.…”

Section: Rh-catalyzed Reaction Of 16-enynesmentioning

confidence: 99%

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Liu,

Xu,

Han

et al. 2024

Adv Synth Catal

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Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products and biologically active pharmaceutical molecules. Over the past few decades, the development of novel and versatile synthetic approaches via cascade cyclization reactions of 1,6‐enynes for the construction of a series of fused and spiro compounds has been the focus of a great deal of research initiatives. These synthesis strategies are peculiarly fascinating in the context of the assembly of a wide array of pharmaceutical molecules, natural products, agrochemicals, and functional materials. In this review, recent developments in the transformations of 1,6‐enynes with diverse coupling reagents are summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed cyclization of 1,6‐enynes; 3) Metal‐free cyclization of 1,6‐enynes; 4) Visible‐light‐induced cyclization of 1,6‐enynes; 5) Electrocatalytic cyclization of 1,6‐enynes.

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Section: Rh-catalyzed Reaction Of 16-enynesmentioning

confidence: 99%

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Liu,

Xu,

Han

et al. 2024

Adv Synth Catal

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“…2.2.1 Rhodium-catalyzed synthesis Wei et al (2021) reported the synthesis of Rh(III)-mediated THF (105) through the stereo/regioselective C-H coupling/ C-terminus Michael addition reaction of N-phenoxy amides (103) with 1,6-enynes (104) (Wei et al, 2021). Under optimal reaction conditions, a series of N-phenoxyacetamides (103) having different functional groups and a variety of 1,6 enynes (104) having alkyl or aryl groups at position 4 gave moderate to good yields (34%-73%).…”

Section: O-heterocyclesmentioning

confidence: 99%

Chemical insights into the synthetic chemistry of five-membered saturated heterocycles—a transition metal–catalyzed approach

Sunbal¹,

Alamzeb²,

Omer³

et al. 2023

Front. Chem.

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Drug design and delivery is primarily based on the hunt for new potent drug candidates and novel synthetic techniques. Recently, saturated heterocycles have gained enormous attention in medicinal chemistry as evidenced by the medicinal drugs listed in the FDA Orange Book. Therefore, the demand for novel saturated heterocyclic syntheses has increased tremendously. Transition metal (TM)–catalyzed reactions have remained the prime priority in heterocyclic syntheses for the last three decades. Nowadays, TM catalysis is well adorned by combining it with other techniques such as bio- and/or enzyme-catalyzed reactions, organocatalysis, or using two different metals in a single catalysis. This review highlights the recent developments of the transition metal–catalyzed synthesis of five-membered saturated heterocycles.

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“…realized C−H alkenylation of various heteroarenes with terminal alkynes under Cp*Rh(III) catalysis [6c] . Recently, cascade annulations of (hetero)arenes with tethered terminal alkynes triggered by Cp*Rh(III)‐catalyzed C−H activation have been reported by the groups of Lin [6d,e] and Yi, [6f] respectively.…”

Section: Introductionmentioning

confidence: 99%

Rhodium(III)‐Catalyzed Regioselective C−H Annulation and Alkenylation of 2‐Pyridones with Terminal Alkynes

Luo

et al. 2022

Adv Synth Catal

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Cp*Rh(III)‐catalyzed regioselective C−H annulation and alkenylation of 2‐pyridones with terminal alkynes have been developed. The cationic Cp*Rh(III) catalytic system containing FeCl3 additive enables annulation of 1‐(2‐pyridyl)‐2‐pyridones with terminal alkynes, providing efficient access to 5,7‐diarylated 2‐quinolinones. The reaction pathway can be switched to alkenylation with [Cp*RhCl2]2 as the catalyst, NaOAc as the additive and HOAc as the solvent, affording C6‐alkenylated 1‐(2‐pyridyl)‐2‐pyridones in high yields. These protocols accommodate a wide range of substrates with good functional group compatibility.

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Rhodium(III)‐Catalyzed Cascade C−H Coupling/C‐Terminus Michael Addition of N‐Phenoxy Amides with 1,6‐Enynes

Cited by 5 publications

References 95 publications

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Recent Advances in Cyclization Reactions of 1,6‐Enynes

Chemical insights into the synthetic chemistry of five-membered saturated heterocycles—a transition metal–catalyzed approach

Rhodium(III)‐Catalyzed Regioselective C−H Annulation and Alkenylation of 2‐Pyridones with Terminal Alkynes

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