Palladium-Catalyzed Annulation of Arynes by<i>o</i>-Halobenzamides: Synthesis of Phenanthridinones

Lu, Chun; Dubrovskiy, Anton V.; Larock, Richard C.

doi:10.1021/jo3016192

Cited by 59 publications

(30 citation statements)

References 74 publications

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“…The Larock group reported two strategies to obtain tricyclic lactams involving intramolecular amide coupling steps ( Scheme 87 b). Fluoride-induced 1,2-elimination of o -(trimethylsilyl)aryl triflates 376 was a practical means to generate highly electrophilic arynes, which after Pd-catalyzed annulation afforded N-substituted phenanthridinones 309 and N -acylcarbazoles. 310 In the presence of Pd(OAc) 2 / L31 , Na 2 CO 3 , and CsF as the fluoride source, o -halobenzamides delivered N-substituted phenanthridinones in 36–87% yield.…”

Section: Amides and Amide Derivativesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Section: Amides and Amide Derivativesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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“…2‐Bromo‐ N ‐isopropylbenzamide (24) : This starting material was prepared using a reported procedure 18…”

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalysed Regioselective Direct Arylations of Heteroarenes by Bromobenzamides: Direct Synthesis of Heteroaryl Benzamides

Chen¹,

Bruneau²,

Dixneuf³

et al. 2013

ChemCatChem

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International audienceThe Pd-catalysed direct arylation of heteroarene C[BOND]H bonds by 2- or 4-bromobenzamides has been achieved. In the presence of KOAc as the base, no C[BOND]N bond formation or C[BOND]C coupling of two bromobenzamides was observed. Both primary and tertiary amides can be employed for C[BOND]C cross-coupling of 4-bromobenzamides with a variety of heteroarenes to give the C5-arylated heteroarenes in good yields by using a low loading (0.5 mol %) of Pd(OAc)2 catalyst. However, no coupling product was observed with 2-bromobenzamide, and a moderate reactivity of 2-bromo-N,N-diethylbenzamide has been observed with 2 mol % PdCl(C3H5)(dppb) (dppb=1,4-bis(diphenylphosphino)butane) as the catalyst. A moderate influence due to the nature of the heteroarene was observed, and thiazoles, thiophenes, furans and pyrroles have been arylated successfully. The reaction of a thiazole with 2-bromo-N-phenylbenzamide led to a six-membered ring product by intramolecular cyclisation, whereas a 2-bromo-N-benzylbenzamide gave the desired intermolecular coupling product

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“…The annulation process has been efficiently used for the synthesis of various bioactive natural products. 36 In 2010, Huang and co-workers reported the carboannulation of arynes with vinyl iodides in the presence of a Pd catalyst. The substrate scope of the optimized protocol was studied on various allyl-substituted iodocycloalkenones 14 and iodofuranones 15 with substituted aryne precursors for the synthesis of dihydrophenanthren-1(2H)-ones 16 and naphtho[2,1-c]furan-3(1H)-ones 17, respectively.…”

Section: Annulation Of Arynesmentioning

confidence: 99%

Transition-Metal-Catalyzed Reactions Involving Arynes

Dhokale

Mhaske

2017

Synthesis

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The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.1 Introduction2 Insertion of Arynes3 Annulation of Arynes4 Cycloaddition of Arynes5 Multicomponent Reactions of Arynes6 Miscellaneous Reactions of Arynes7 Total Synthesis of Natural Products Using Arynes8 Conclusion

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Palladium-Catalyzed Annulation of Arynes byo-Halobenzamides: Synthesis of Phenanthridinones

Cited by 59 publications

References 74 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Palladium‐Catalysed Regioselective Direct Arylations of Heteroarenes by Bromobenzamides: Direct Synthesis of Heteroaryl Benzamides

Transition-Metal-Catalyzed Reactions Involving Arynes

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