Indium-Catalyzed Reductive Coupling Enabled Efficient Synthesis of Acylphosphine Oxides and Diphosphines

Xu，Dongdong; Jin，Ming Yu; Chen，Yu; Han，Dingnuo; Tao，Lizhi; Xing，Xiangyou

2024-03-01

10.1021/acscatal.3c05947

ACS Catalysis   影响因子和分区

2155-5435

The unique low level of the ionization potential of indium(0) to indium(I) makes it an appealing metal for organic synthesis. Here, we present an indium-catalyzed reductive cross-coupling between chlorophosphines (RPCl) or dichlorophosphines (RPCl) with acyl chlorides (RCOCl). This one-pot approach, using indium-catalysis followed by oxidation, generates a variety of mono- or bis-acylphosphine oxides in good yields. Additionally, this protocol offers a convenient pathway to obtain the photoinitiators, Luricin TPO and IRGACURE 819, that are widely used in the industry. Experimental and computational studies indicate the intermediacy of phosphorus-based radical species that dimerize to diphosphines, which then couple with acyl chlorides through a four-membered transition state. Furthermore, we also explore indium-catalyzed reductive homocoupling of RPCl or RPCl, which provides facile access to various P-P bond formations.

acylphosphine oxide diphosphine indium photoinitiator reductive coupling

SCI ; EI

英语

第一 ; 通讯

20240815616805

Chlorine compounds ; Indium compounds ; Ionization potential

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Atomic and Molecular Physics:931.3

2-s2.0-85185581001

Scopus

Shenzhen Grubbs Institute and Department of Chemistry,Southern University of Science and Technology,Shenzhen,518055,China

Xu，Dongdong,Jin，Ming Yu,Chen，Yu,et al. Indium-Catalyzed Reductive Coupling Enabled Efficient Synthesis of Acylphosphine Oxides and Diphosphines[J]. ACS Catalysis,2024,14(5):3241-3247.

Xu，Dongdong,Jin，Ming Yu,Chen，Yu,Han，Dingnuo,Tao，Lizhi,&Xing，Xiangyou.(2024).Indium-Catalyzed Reductive Coupling Enabled Efficient Synthesis of Acylphosphine Oxides and Diphosphines.ACS Catalysis,14(5),3241-3247.

Xu，Dongdong,et al."Indium-Catalyzed Reductive Coupling Enabled Efficient Synthesis of Acylphosphine Oxides and Diphosphines".ACS Catalysis 14.5(2024):3241-3247.