Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans

Erguven, Huseyin; Zhou, Cuihan; Arndtsen, Bruce A.

doi:10.1039/d1sc04088j

Cited by 4 publications

References 87 publications

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Palladium‐Catalyzed Cyclizative Borylation of Allenyl Ketones through Carbene Boryl Migratory Insertion: Access to Densely Substituted Furyl Boronates

Wang

2023

Chemistry A European J

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Herein the palladium-catalyzed cyclizative borylation of allenyl ketones with diboron compounds is reported which involves the carbene boryl migratory insertion as the key step. This reaction features mild conditions, good functional group tolerance and broad substrate scope. Thus, it represents an efficient methodology for the assembly of diverse tri-substituted furyl boronates. In addition, a series of transformations of the resultant multi-substituted furyl boronates were conducted to provide various densely substituted furan derivatives in good yields, further illustrating the potential synthetic utility of this methodology.

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Palladium‐Catalyzed Cyclizative Borylation of Allenyl Ketones through Carbene Boryl Migratory Insertion: Access to Densely Substituted Furyl Boronates

Wang

2023

Chemistry A European J

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Catalytic Intramolecular Ketone Haloacylation Enabled Stereoselective Heterolytic Cleavage of Cyclopropyl Ketones with Enhanced Reactivity and Regioselectivity beyond Electronics

Lei,

Wang,

Wang

2024

Org. Lett.

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By integration of oxocarbenium activation and Lewis acid coordination activation via conformational proximity-driven, Pd(II)-or Cu(I)-catalyzed intramolecular ketone haloacylation, regio-and stereoselective heterolytic ring-opening 1,5-haloacylation of cyclopropyl ketones, including those with weak single alkyl donors, has been developed for the synthesis of valuable αquaternary halo-γ-butenolides. The vicinal carboxylic acid and ketone acceptors are no longer just spectator activators. Further, this reaction delivers a constant regioselectivity regardless of the electronic nature of substituents, even the malonate.

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Tervalent phosphorus acid derivatives

Pereira,

Carrilho,

Calvete

2024

Organophosphorus Chemistry

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This chapter covers the most relevant literature published during the year 2021, related to tervalent phosphorus acid derivatives. Some of the most relevant concepts are reported, regarding synthetic methodologies to phosphorus amides (aminophosphines, phosphoramidites and diamidophosphites), phosphorus esters (phosphinites, phosphonites and phosphites), and mixed phosphorus compounds bearing two different tervalent phosphorus moieties. A critical selection of their applications is briefly assessed, with an emphasis on the catalytic applications of ligands and metal complexes.

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Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans

Abstract: A new class of phosphorus-containing 1,3-dipole can be generated by the multicomponent reaction of aldehydes, acid chlorides and the phosphonite PhP(catechyl). These 1,3-dipoles are formally cyclic tautomers of simple Wittig-type...

Cited by 4 publications

References 87 publications

Palladium‐Catalyzed Cyclizative Borylation of Allenyl Ketones through Carbene Boryl Migratory Insertion: Access to Densely Substituted Furyl Boronates

Palladium‐Catalyzed Cyclizative Borylation of Allenyl Ketones through Carbene Boryl Migratory Insertion: Access to Densely Substituted Furyl Boronates

Catalytic Intramolecular Ketone Haloacylation Enabled Stereoselective Heterolytic Cleavage of Cyclopropyl Ketones with Enhanced Reactivity and Regioselectivity beyond Electronics

Tervalent phosphorus acid derivatives

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