Stereoselective Synthesis of Enamides through Palladium‐Catalyzed Oxidative Amidation of Conjugated Olefins with 2‐Pyridones

Zhao, Shuai; Lu, Bin-Wei; Bao, Ning; Yin, Zi-Jian; Qian, Mingcheng; Chen, Lin; Geng, Meiyu; Lin, Yuanyuan; Chen, Xin

doi:10.1002/ejoc.202201239

Cited by 3 publications

(1 citation statement)

References 60 publications

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“…This protocol employed Pd(OAc) 2 as catalyst and AgTFA as oxidant, providing a series of N ‐alkenylated 2‐pyridones 132 in the decent yields (Scheme 36). [74] Unfortunately, the styrenes delivered low yields.…”

Section: N‐functionalization Of 2‐hydroxypyridinesmentioning

confidence: 99%

2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis

Li,

Wang,

2023

Eur J Org Chem

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2‐Hydroxypyridines have emerged as versatile nucleophiles in organic synthesis. The N‐ and O‐functionalization of 2‐hydroxypyridines affords straightforward and practical methods for the construction of N‐substituted 2‐pyridones and O‐substituted 2‐hydroxypyridines, which are important structural motifs in numerous natural products, pharmaceuticals and biologically active compounds. Nonetheless, the competition between N‐ and O‐functionalization of 2‐hydroxypyridines presents an inevitable and formidable challenge. In the past few decades, chemoselective N‐ and/or O‐functionalization of 2‐hydroxypyridines has received extensive attention from the synthetic community, resulting in the development of elegant and effective strategies to address this chemoselectivity. This review provides a summary of recent advancements in the realm of transition‐metal and organo‐catalyzed, as well as visible‐light promoted chemoselective functionalization of 2‐hydroxypyridines, including N‐alkylation, N‐allylation, N‐arylation, N‐alkenylation, O‐alkylation, O‐allylation, O‐arylation, and O‐alkenylation.

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Section: N‐functionalization Of 2‐hydroxypyridinesmentioning

confidence: 99%

2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis

Li,

Wang,

2023

Eur J Org Chem

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Regioselective Carbozincation and Further Functionalization of Allenamides Catalyzed by an N‐Heterocyclic Carbene (NHC)‐Copper Complex

Takimoto,

Hou

2023

Asian J Org Chem

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An efficient protocol for the carbozincation of allenamides with dialkylzinc reagents catalyzed by an NHC‐Cu complex has been developed. This protocol could provide alkenylzinc species introducing the alkyl group to γ‐position and the zinc component to β‐position of the allenamides in a regio‐ and stereoselective manner. The resulting alkenylzinc species can undergo further C‐C bond‐forming reactions, such as allylation, arylation, and benzoylation, affording a variety of β,β‐disubstituted enamides with well‐controlled configurations of the two substituents. Moreover, the chiral allenamide synthesized via this method can be converted to a chiral aminocyclopropane derivative. In view of the high regio‐ and stereoselectivity and the convenient one‐pot procedure, this sequential transformation protocol offers a potentially useful method for synthesizing multi‐substituted enamides, which are important compounds in synthetic organic chemistry.

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Palladium-catalyzed vinylation of indoles with vinyl ethers via deoxygenative coupling

Wang,

Li,

et al. 2024

Sci. China Chem.

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Stereoselective Synthesis of Enamides through Palladium‐Catalyzed Oxidative Amidation of Conjugated Olefins with 2‐Pyridones

Cited by 3 publications

References 60 publications

2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis

2‐Hydroxypyridines as N‐ and O‐Nucleophiles in Organic Synthesis

Regioselective Carbozincation and Further Functionalization of Allenamides Catalyzed by an N‐Heterocyclic Carbene (NHC)‐Copper Complex

Palladium-catalyzed vinylation of indoles with vinyl ethers via deoxygenative coupling

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