An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides

An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.

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Palladium-catalyzed dehydrogenative coupling of terminal alkynes with secondary phosphine oxides

Chemical Communications ◽

10.1039/c4cc09567g ◽

2015 ◽

Vol 51 (17) ◽

pp. 3549-3551 ◽

Cited By ~ 32

Author(s):

Jia Yang ◽

Tieqiao Chen ◽

Yongbo Zhou ◽

Shuangfeng Yin ◽

Li-Biao Han

Keyword(s):

Reaction Mechanism ◽

Palladium Acetate ◽

Secondary Phosphine ◽

Terminal Alkynes ◽

Phosphine Oxides ◽

Dehydrogenative Coupling ◽

Palladium Catalyzed ◽

High Yields

The palladium-catalyzed dehydrogenative coupling of alkynes with secondary phosphine oxides is developed. Thus, in the presence of a silver additive, palladium acetate could efficiently catalyze the dehydrocoupling of secondary phosphine oxides with a variety of alkynes to produce the corresponding alkynylphosphine oxides in high yields. A reaction mechanism is proposed.

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Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

10.26434/chemrxiv.7796603.v1 ◽

2019 ◽

Cited By ~ 1

Author(s):

Arumugavel Murugan ◽

Venkata Nagarjuna Babu ◽

Nagaraj Sabarinathan ◽

Sharada Duddu. S

Keyword(s):

Transition Metal ◽

Visible Light ◽

Practical Approach ◽

Hypervalent Iodine ◽

Radical Mechanism ◽

Photoredox Catalysis ◽

Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

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A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

Organic & Biomolecular Chemistry ◽

10.1039/d1ob01045j ◽

2021 ◽

Author(s):

Tao Fan ◽

Yan Liu ◽

Caina Jiang ◽

Yanli Xu ◽

Yan-Yan Chen

Keyword(s):

Free Radical ◽

Transition Metal ◽

Cascade Reaction ◽

Phosphine Oxides ◽

Metal Free ◽

Mild Conditions ◽

Xanthene Derivatives ◽

Reaction Proceeds ◽

Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

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