Yuxing Gao

Copper-Catalyzed Aerobic Oxidative Coupling of Terminal Alkynes with H-Phosphonates Leading to Alkynylphosphonates

Copper catalyzed the aerobic oxidative coupling of terminal alkynes with H-phosphonates to afford alkynylphosphonates in high yields.

Nickel-Catalyzed C-P Cross-Coupling of Arylboronic Acids with P(O)H Compounds

A novel and efficient Ni-catalyzed coupling of a wide range of arylboronic acids with H-phosphites, H-phosphinate esters, and H-phosphine oxides has been developed, providing a general and powerful tool for the synthesis of various aryl-phosphorus compounds, especially for valuable triarylphosphine oxides, in good to excellent yield. This protocol is the first Ni-catalyzed C-P bond-forming reaction between arylboronic acids and P(O)H compounds.

Copper-Catalyzed Decarboxylative C-P Cross-coupling of Alkynyl Acids with H-phosphine Oxides: A Facile and Selective Synthesis of (E)-1-Alkenylphosphine Oxides

A novel and efficient copper-catalyzed decarboxylative cross-coupling of alkynyl acids for the stereoselective synthesis of E-alkenylphosphine oxides has been developed. In the presence of 10 mol % of CuCl without added ligand, base, and additive, various alkynyl acids reacted with H-phosphine oxides to afford E-alkenylphosphine oxides with operational simplicity, broad substrate scope, and the stereoselectivity for E-isomers.

Experimental and Theoretical Study on Palladium-Catalyzed C-P Bond Formation via Direct Coupling of Triarylbismuths with P(O)-H Compounds

A novel and highly efficient Pd-catalyzed cross-coupling of triarylbismuths with a variety of P(O)-H compounds has been developed that proceeds smoothly without exclusion of moisture or air and provides a general and powerful tool for the preparation of various valuable arylphosphonates, arylphosphinates, and arylphosphine oxides, with high atom-economy, operational simplicity of the procedure, and good to high yield. The coupling reaction is the first example of transition-metal-catalyzed C-P bond construction using triarylbismuth compounds as substrates. DFT calculations reveal that C-P bond formation is the rate-determing step.

Nickel-Catalyzed Decarboxylative C-P Cross-Coupling of Alkenyl Acids with P(O)H Compounds.

The first nickel-catalyzed decarboxylative C-P coupling of a wide range of alkenyl acids with various P(O)H compounds, especially for H-phosphonates, has been developed, affording a versatile and efficient tool for the preparation of valuable (E)-1-alkenylphosphonates, (E)-1-alkenylphosphinate oxides, and (E)-1-alkenylphosphine oxides with high stereoselectivity and broad substrate applicability. DFT calculation revealed that the phosphine ligand exhibits better catalytic performance than the nitrogen ligand in the reductive elimination step owing to the stronger nucleophilicity and larger size.

Copper-catalyzed synthesis of α-hydroxy phosphonates from H-phosphonates and alcohols or ethers

Chinese National Natural Science Foundation [21173178, 21202135, 21232005]; National Basic Research Program of China [2012CB821600]; [TJAB-2009-023]

Palladium-catalyzed Suzuki cross-coupling of arylhydrazines via C-N bond cleavage.

The first example of Pd-catalyzed Suzuki cross-coupling of readily available arylhydrazines with arylboronic acids via C-N bond cleavage was developed under air, affording various biaryl compounds with broad substrate applicability and moderate to good yields. Moreover, the rigorous exclusion of air/moisture is not required in these transformations. Thus, the protocol represents a simple and efficient procedure to access biaryl compounds.

Cs2CO3-promoted one-pot synthesis of alkynylphosphonates, -phosphinates, and -phosphine oxides

A novel and efficient Cs2CO3-promoted phosphorylation or phosphinylation of various 1,1-dibromo-1-alkenes with readily available trialkyl phosphites, ethyl diphenylphosphinite, or diethyl phenylphosphonite has been developed under metal-free conditions, providing a practical and powerful tool for one-pot synthesis of valuable alkynylphosphonates, -phosphinates, and -phosphine oxides in good to excellent yields.

Palladium-catalyzed air-based oxidative coupling of arylboronic acids with H-phosphine oxides leading to aryl phosphine oxides

We present a novel and highly efficient methodology that allows for the construction of C-P bonds via the palladium-catalyzed air-based oxidative coupling of various commercially available arylboronic acids with easily oxidized H-phosphine oxides leading to valuable aryl phosphine oxides, particularly triarylphosphine oxides, with the use of air as the green oxidant, broad substrate applicability and good to excellent yields. The described catalytic system should be an efficient complement to the Chan-Lam type reaction and be useful in synthetic programs.

K2S2O8-mediated metal-free direct P–H/C–H functionalization: a convenient route to benzo[b]phosphole oxides from unactivated alkynes

The first metal-free, facile and K2S2O8-mediated radical addition/cyclization of unactivated alkynes with diarylphosphine oxides has been developed, affording a general and practical procedure to construct valuable benzo[b]phosphole oxides via sequential P–H/C–H functionalization.