Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C–H Alkenylation of Pyridinium Salts with Alkynes

Li, Wenjing; Tang, Juan; Li, Shun; Zheng, Xueli; Xu, Bin; Jiang, Weidong; Fu, Haiyan; Li, Ruixiang; Chen, Hua

doi:10.1021/acs.orglett.0c02679

Cited by 26 publications

(7 citation statements)

References 61 publications

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“…A plausible mechanism is depicted in Scheme 11. 76 Minami, Hiyami et al established a dual-metal catalytic system involving Pd/Cu catalysts for the cross-coupling of bromoarenes 26 with aryl(trialkyl)silanes 51. Significantly, this method enabled the cross-coupling of various aryl(trialkyl)silanes [e.g., trimethyl, triethyl, triisopropyl, and tertbutyldimethyl aryl silanes] with various aryl bromides 26 to deliver the anticipated coupling products 52.…”

Section: Cu/pd-catalysed C(sp 2 )-C(sp 2 ) Bond Formationmentioning

confidence: 99%

Recent Applications on Dual-Catalysis for C–C and C–X Cross-Coupling Reactions

Kishore¹,

Sreenivasulu²,

Dapkekar³

et al. 2022

SynOpen

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Coupling reactions stand amid the most significant reactions in synthetic organic chemistry. Of late, these coupling strategies are being viewed as a versatile synthetic tool for a wide range of organic transformations in many sectors of chemistry, ranging from indispensable synthetic scaffolds and natural products of biological significance to novel organic materials. Further, the usage of dual-catalysis in accomplishing various interesting cross-coupling transformations is an emerging field in synthetic organic chemistry, owing to their high catalytic performance rather than the usage of a single catalyst. In recent years, synthetic organic chemists have given considerable attention to hetero-dual catalysis, wherein these catalytic systems have been employed for the construction of versatile carbon-carbon [C(sp3)–C(sp3), C(sp3)–C(sp2), C(sp2)–C(sp2), etc.] and carbon-heteroatom (C-N, C-O, C-P, C-S, etc.) bonds. Therefore, in this mini-review, we are emphasizing recently developed various cross-coupling reactions catalysed by transition-metal dual-catalysis (i.e., using palladium and copper catalysts, and by omitting the reports on photoredox/metal catalysis).

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Section: Cu/pd-catalysed C(sp 2 )-C(sp 2 ) Bond Formationmentioning

confidence: 99%

Recent Applications on Dual-Catalysis for C–C and C–X Cross-Coupling Reactions

Kishore¹,

Sreenivasulu²,

Dapkekar³

et al. 2022

SynOpen

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“…In 2020, Fu, Chen, and co-workers investigated selective C2-alkenylation of pyridines with internal alkynes via the pyridinium salt activation strategy using Cu/Pd as dual catalysis. [47] Besides the functionalization of pyridines, they also reported one example of the alkylation of 2,2'bipyridine (Scheme 25). They employed a bimetallic system Pd(OAc) 2 associated with CuBr to functionalized 1-methyl-[2,2'-bipyridin]-1-ium salt.…”

Section: Cà H Bond Functionalization Of Activated Bipyridinesmentioning

confidence: 99%

Synthesis of 2,2’‐Bipyridines through Catalytic C−C Bond Formations from C−H Bonds

2021

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The present review describes the homogenous catalytic methodologies for the synthesis of 2,2’‐bipyridines involving C−C bond formation from C−H bond. There are three main approaches to build well‐decorated 2,2’‐bipyridines from C−H bond cleavage: i) the formation of C2−C2′ bond by the dimerization of (activated) pyridines, ii) the C−H bond heteroarylation of activated pyridine, or iii) the late‐stage functionalization of (activated) 2,2’‐bipyridines including photoredox processes. Besides the scope and limitation of each methodologies, the relevant mechanisms of reaction are also discussed.

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“…In 2020, Fu, Chen, and co-workers investigated selective C2-alkenylation of pyridines with internal alkynes via the pyridinium salt activation strategy using Cu/Pd as dual catalysis. [47] Besides the functionalization of pyridines, they also reported one example of the alkylation of 2,2'-bipyridine (Scheme 25). They employed a bimetallic system Pd(OAc)2 associated with CuBr to functionalized 1methyl-[2,2'-bipyridin]-1-ium salt.…”

Section: C-h Bond Functionalization Of Activated Bipyridinesmentioning

confidence: 99%

Front Cover: Synthesis of 2,2’‐Bipyridines through Catalytic C−C Bond Formations from C−H Bonds (Eur. J. Org. Chem. 39/2021)

2021

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The Front Cover shows – drawn in a cartoon‐style illustration – the different strategies to synthesize 2,2′‐bipyridines involving a C−H bond functionalization step. On the left side, the three approaches are inlaying in green lines. The catalysts (transition metal) are drawn in a bubble to illustrate the challenge of maintaining their catalytic activity while 2,2’‐bipyridines can coordinate and affect their properties. On the right side, the 2,2′‐bipyridine is designed as an allegory featuring a pink Cardoon flower for ligands and a bee for metals, showing their mutual bonding. Anne‐Sophie Pochet is thanked for taking the original photography on which this cover is built. More information can be found in the Minireview by J.‐F. Soulé et al.

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Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C–H Alkenylation of Pyridinium Salts with Alkynes

Cited by 26 publications

References 61 publications

Recent Applications on Dual-Catalysis for C–C and C–X Cross-Coupling Reactions

Recent Applications on Dual-Catalysis for C–C and C–X Cross-Coupling Reactions

Synthesis of 2,2’‐Bipyridines through Catalytic C−C Bond Formations from C−H Bonds

Front Cover: Synthesis of 2,2’‐Bipyridines through Catalytic C−C Bond Formations from C−H Bonds (Eur. J. Org. Chem. 39/2021)

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