Palladium‐Catalyzed Electrophilic Functionalization of Pyridine Derivatives through Phosphonium Salts

Che, Yuanyuan; Yue, Yanni; Lin, Ling-Zhi; Pei, Bingbing; Deng, Xuezu; Feng, Chao

doi:10.1002/anie.202006724

Cited by 46 publications

(23 citation statements)

References 95 publications

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“…Similar hypotheses and observations were made by Su and co-workers for palladium and silver mediated decaboxylative C-H arylations of thiophenes, stressing the importance of a sufficiently fast palladium process compared to the generation of the silver aryl species. [31,32] We envisioned optimization of the temperature and catalytic system to be feasible handles for addressing this issue.…”

Section: Initial Observations and Optimizationmentioning

confidence: 99%

Cross-coupling Reactions of Monosubstituted Tetrazines

Hoff¹,

Schnell²,

Tomio³

et al. 2021

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<div><div><div><p>A fast and mild method for the Pd-catalyzed cross-coupling reaction of monosubstituted 3-bromo-1,2,4,5-tetrazine is presented. Investigation of silver-based additives revealed that Ag2CO3 is the optimal mediator, enabling the process without the need for strong bases or high temperatures. Electronic modification of the classical 1,1′- bis(diphenylphosphine)ferrocene (dppf) ligand proved to be a powerful strategy in tailoring the catalytic system to the requirements set by the process. Under the optimized conditions a scope comprising a variety of alkyl-, heteroatom-, and halide substituted aryl- and heteroaryl-tetrazines were prepared in good to excellent yields (29 examples, up to 87% yield). This method constitutes the first example of a direct cross-coupling reaction of monosubstituted tetrazines.</p></div></div></div>

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Section: Initial Observations and Optimizationmentioning

confidence: 99%

Cross-coupling Reactions of Monosubstituted Tetrazines

Hoff¹,

Schnell²,

Tomio³

et al. 2021

Preprint

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“…These observations are in agreement with intermediary silver aryl species, which have been described in the literature. 18 The amounts of Ag 2 CO 3 and boronic acid were minimized to 1.0 and 1.5 equiv, respectively, which provided the best results (Table 1, entries 5−8). When Ag 2 CO 3 was omitted from the cross-coupling reactions, or when it was exchanged with Na 2 CO 3 , no product was formed (Table S6).…”

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confidence: 99%

Cross-Coupling Reactions of Monosubstituted Tetrazines

et al. 2021

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“…Utilisation of the chemistry of main group elements to perform cross-coupling reactions,r ather than relying on precious transition metals,c ould become ap opular area for synthetic chemists to explore, [132] especially as more sustainable and greener solutions are sought.…”

Section: Main Group Ligand Couplingsmentioning

confidence: 99%

The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations

et al. 2020

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Xinlan Cook received her MChem degree from the University of York in 2017, completing her master's thesis during ayear-long placementa tF.Hoffmann-La Roche (Basel, Switzerland),synthesising novel molecules for the treatment of Alzheimer's disease. She is now completing her doctoral research in the group of Prof. M. C. Willis at the University of Oxford, investigating novel reagents for C(sp 2 )ÀC(sp 2 )d esulfinative cross-coupling reactions. Antoine de Gombert graduated from Chimie ParisTech and UniversitØ Pierre et Marie Curie with aDiplôme d'IngØnieur and MSci. After working on visible light catalysis at CSIRO (Australia), he completed a6 -month internship at F. Hoffmann-La Roche in Switzerland. He is currently aPhD student with Prof. M. C. Willis at the University of Oxford, where his research focuses on the mechanistica spects of palladium-catalysed desulfinative cross-coupling reactions. Janette McKnight obtained her MChem degree from the University of Bath in 2017. During this time, she undertook an industrial placementy ear in process chemistry at GSK Stevenage, before returning to complete afinal year project in the field of CÀH activation with Prof. C. Frost. She moved to the University of Oxford for postgraduate study,where she is currently working on C(sp 2 )ÀC(sp 3 )desulfinativec ross-coupling reactions under the supervision of Prof. M. C. Willis.

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Palladium‐Catalyzed Electrophilic Functionalization of Pyridine Derivatives through Phosphonium Salts

Cited by 46 publications

References 95 publications

Cross-coupling Reactions of Monosubstituted Tetrazines

Cross-coupling Reactions of Monosubstituted Tetrazines

Cross-Coupling Reactions of Monosubstituted Tetrazines

The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations

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