N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation of symmetric dialkyl ketones with aryl chlorides

• Published in: Inorganica Chimica Acta Vol. 423; pp. 106 - 108
• Main Authors: Xiao, Zheng-Kang, Yin, Hui-Ying, Lu, Jian-Mei
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.11.2014
• Subjects: Aryl chloride; N-Heterocyclic carbene-palladium complex; Symmetric dialkyl ketone; Synthetic method; α-Arylation; HSPJCYFDCGXPRJ-UHFFFAOYSA-N; α-Arylation; QOVGUJZOLRHKOS-UHFFFAOYSA-N; XFIVLHFLUVDRKA-UHFFFAOYSA-N; AUXHANWHNFFYEA-UHFFFAOYSA-N; ZWTGOWUKMSTVLI-UHFFFAOYSA-N; GOMICFXDZKVKCM-UHFFFAOYSA-N; VLVWHUDVJQJNPL-UHFFFAOYSA-N; MYNICRSHUXZJTN-UHFFFAOYSA-N; PKPLYSUJEYYYEL-UHFFFAOYSA-N; JQBRSPRLCBZVPS-UHFFFAOYSA-N; CHUWJTKWUFKEHE-UHFFFAOYSA-N; YXZMTORWBBIGGG-UHFFFAOYSA-N; DTLQGRAGKDDPQT-UHFFFAOYSA-N; YFCSLOSDCAMOBB-UHFFFAOYSA-N; QJWCIWHOEWRMKZ-UHFFFAOYSA-N; N-Heterocyclic carbene-palladium complex; BGIDSTUGOFJHAR-UHFFFAOYSA-N; Symmetric dialkyl ketone; JHUIIBLCHSQNDC-UHFFFAOYSA-N; QSXVCRXXVJWXDV-UHFFFAOYSA-N; Aryl chloride; RCYYNQGKCMNJFS-UHFFFAOYSA-N; TWBHPBMFUUJPTR-UHFFFAOYSA-N; CWHQJWMAKVLAAI-UHFFFAOYSA-N; OWDHNYUHCPSQFR-UHFFFAOYSA-N; UYXZZTGJCIWPJY-UHFFFAOYSA-N; DUINWNWBXWNDOO-UHFFFAOYSA-N; Synthetic method
• ISSN: 0020-1693; 1873-3255
• DOI: 10.1016/j.ica.2014.07.061

N-Heterocyclic carbene-Pd(II)-1-methylimidazole complex 1 showed efficient catalytic activity toward α-arylation of symmetric dialkyl ketones under mild conditions. When the ratio between aryl chlorides and ketones was 1:2, mono-arylated products can be obtained in good to high yields as the sole; while that of aryl chlorides and ketones was changed to 1:0.7, di- and mono-arylated products were obtained in good to high total yields, with the former as the major. [Display omitted] •NHC-Pd(II) complex showed high activity in α-arylation of symmetric dialkyl ketones.•Mono-arylated products were formed in good to high yields under suitable conditions.•All reactions gave the desired α-arylated products in good to high yields. N-Heterocyclic carbene-palladium(II)-1-methylimidazole [NHC-Pd(II)-Im] complex 1 showed efficient catalytic activity toward α-arylation of symmetric dialkyl ketones under mild conditions. It was found that the ratio of aryl chlorides and ketones drastically affected the reaction. When the ratio of aryl chlorides and ketones was 1:2, mono-arylated products can be obtained in good to high yields as the sole; while that of aryl chlorides and ketones was changed to 1:0.7, di- and mono-arylated products were obtained in good to high total yields at the same time, with the former as the major.