Identification of a potent palladium-aryldiphosphine catalytic system for high-performance carbonylation of alkenes

Kang Zhao, Hongli Wang, Teng Li, Shujuan Liu, Enrico Benassi (), Xiao Li, Yao Yao, Xiaojun Wang, Xinjiang Cui () and Feng Shi ()
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Kang Zhao: Chinese Academy of Sciences
Hongli Wang: Chinese Academy of Sciences
Teng Li: Chinese Academy of Sciences
Shujuan Liu: Chinese Academy of Sciences
Enrico Benassi: Novosibirsk State University
Xiao Li: Nanjing Chengzhi Clean Energy Co., LTD.
Yao Yao: Nanjing Chengzhi Clean Energy Co., LTD.
Xiaojun Wang: Nanjing Chengzhi Clean Energy Co., LTD.
Xinjiang Cui: Chinese Academy of Sciences
Feng Shi: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract The development of stable and efficient ligands is of vital significance to enhance the catalytic performance of carbonylation reactions of alkenes. Herein, an aryldiphosphine ligand (L11) bearing the [Ph2P(ortho-C6H4)]2CH2 skeleton is reported for palladium-catalyzed regioselective carbonylation of alkenes. Compared with the industrially successful Pd/1,2-bis(di-tert-butylphosphinomethyl)benzene catalyst, catalytic efficiency catalyzed by Pd/L11 on methoxycarbonylation of ethylene is obtained, exhibiting better catalytic performance (TON: >2,390,000; TOF: 100,000 h−1; selectivity: >99%) and stronger oxygen-resistance stability. Moreover, a substrate compatibility (122 examples) including chiral and bioactive alkenes or alcohols is achieved with up to 99% yield and 99% regioselectivity. Experimental and computational investigations show that the appropriate bite angle of aryldiphosphine ligand and the favorable interaction of 1,4-dioxane with Pd/L11 synergistically contribute to high activity and selectivity while the electron deficient phosphines originated from electron delocalization endow L11 with excellent oxygen-resistance stability.

Date: 2024
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DOI: 10.1038/s41467-024-46286-9

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