Deoxygenative Hetero- and Carbofunctionalizations of Diarylketones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 8157 - 8167

Published: May 10, 2024

Direct transformations of diarylketones to hetero- and carbofunctionalized diarylmethanes have been developed. The reactions involve a phospha-Brook rearrangement diphenylphosphine oxide with diarylketones, followed by substitutions various nucleophiles such as amides, amines, phenols, thiols, diborylmethane under palladium catalysis afford the corresponding functionalized in reductive manner.

Language: Английский

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Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 28, 2025

Herein, we present a versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones from aldehydes arenes. This involves: (1) regioselective Ar-H alkylation to form benzhydrylphosphonium salts via one-pot, four-component reaction with simple reagents (2) chemoselective reductions or oxidations of the benzylic C-P bond. Notably, D2O yield fully deuterated diarylmethanes. high-yielding, straightforward approach offers valuable building blocks enables novel transformations academic pharmaceutical research.

Language: Английский

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Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives

Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6396 - 6400

Published: Aug. 23, 2023

Herein, we report a straightforward practical method for efficiently obtaining diverse range of thiophosphonium salts. This involves the direct coupling commercially available thiols and aldehydes with Ph3P TfOH. The setup is simple carried out in metal-free manner. synthetic utility these salts demonstrated through various examples C-P bond functionalizations, enabling synthesis thioether, deuterated thioester, dithioester derivatives. These products, which serve as valuable building blocks, are obtained high yields.

Language: Английский

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Heteroarylation of Organophosphonium Salts with Indoles in Water: Synthesis of Symmetrical and Unsymmetrical 3,3'‐Bisindolylmethane Derivatives

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 16, 2024

Abstract A method for the synthesis of symmetrical and unsymmetrical 3,3′‐bis(indolyl)methanes (3,3′‐BIMs) has been developed through direct heteroarylation indolyl‐containing di(hetero)aryl phosphonium salts with indole derivatives in aqueous media. This metal‐free reaction proceeds smoothly under mild conditions, eliminating need hazardous solvents expensive additives/catalysts typically used conventional routes, thereby highlighting synthetic practicality efficiency process. The success this approach is largely attributed to role water as a promoter, facilitating C−P bond functionalization salts. Furthermore, demonstrates broad substrate scope, good functional group tolerance, excellent scalability. Moreover, protocol can also be extended triindolylmethane compound diarylmethylated indole.

Language: Английский

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Practical Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioe-ster Derivatives

Published: July 13, 2023

Herein, we report a straightforward method for efficiently obtaining diverse range of thiophosphonium salts. This involves the direct coupling commercially available thiols and aldehydes with Ph3P TfOH. The setup is simple carried out in metal-free manner. synthetic utility these salts demonstrated through various examples C–+P bond functionalizations, enabling synthesis thioether, deuterated-thioether, thioester, dithioester derivatives. These products, which serve as valuable building blocks, are obtained high yields.

Language: Английский

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