Simultaneous Reduction of Aldehyde Group to Hydroxymethyl Group in Palladium-catalyzed Suzuki Cross-coupling Reaction

doi:10.1007/s40242-014-3562-8

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (4): 614-618.doi: 10.1007/s40242-014-3562-8

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Simultaneous Reduction of Aldehyde Group to Hydroxymethyl Group in Palladium-catalyzed Suzuki Cross-coupling Reaction

WANG Yingchun¹, LI Xiuying², LI Yajun², PAN Yingming², CHENG Keguang², WANG Hengshan²

1. College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, P. R. China;
2. Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education, School of Chemistry &Chemical Engineering, Guangxi Normal University, Guilin 541004, P. R. China

Online:2014-08-01 Published:2014-03-05
Contact: WANG Yingchun, WANG Hengshan E-mail:wangyingchun2014@163.com;whengshan@163.com
Supported by:
Supported by the Basic Research and Development Program of China(No.2011CB512005) and the National Natural Science Foundation of China(Nos.21362002, 41206077, 81260472).

Abstract

Abstract:

The authors presented an efficient method for the palladium-catalyzed Suzuki cross-coupling reaction with the simultaneous reduction of the aldehyde to a hydroxymethyl group. This method allows halide substituted aryl aldehydes to readily react with arylboronic acids, producing polycyclic aromatic alcohols in moderate to good yields. The reaction was catalyzed by Pd(OAc)₂(3%, molar fraction) at 150℃ in the presence of 6%(molar fraction) 1,4-diazabicyclo[2.2.2]octane(DABCO) and 3 times the molecular weight of K₂CO₃ in the mixture solvent of N,N-dimethylformamide(DMF)/H₂O[V(DMF):V(H₂O)=5:1].

Key words: Palladium, Suzuki cross-coupling, Reduction, Polycyclic aromatic alcohol

WANG Yingchun, LI Xiuying, LI Yajun, PAN Yingming, CHENG Keguang, WANG Hengshan. Simultaneous Reduction of Aldehyde Group to Hydroxymethyl Group in Palladium-catalyzed Suzuki Cross-coupling Reaction[J]. Chemical Research in Chinese Universities, 2014, 30(4): 614-618.

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Simultaneous Reduction of Aldehyde Group to Hydroxymethyl Group in Palladium-catalyzed Suzuki Cross-coupling Reaction

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