Hydrogen auto-transfer under aerobic oxidative conditions: Efficient synthesis of saturated ketones by aerobic C-C cross-coupling of primary and secondary alcohols catalyzed by a Au6Pd/resin catalyst

doi:10.1016/S1872-2067(16)62511-1

Chinese Journal of Catalysis ›› 2016, Vol. 37 ›› Issue (10): 1764-1770.DOI: 10.1016/S1872-2067(16)62511-1

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Hydrogen auto-transfer under aerobic oxidative conditions: Efficient synthesis of saturated ketones by aerobic C-C cross-coupling of primary and secondary alcohols catalyzed by a Au₆Pd/resin catalyst

Maoxiang Zhou^a,b, Leilei Zhang^a, Jeffrey T. Miller^c, Xiaofeng Yang^a, Xiaoyan Liu^a, Aiqin Wang^a, Tao Zhang^a

a State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;
b University of Chinese Academy of Sciences, Beijing 100049, China;
c CSE, Argonne National Laboratory, Argonne, IL 60439, USA

Received:2016-04-15 Revised:2016-06-30 Online:2016-10-21 Published:2016-10-22
Contact: Aiqin Wang, Tao Zhang
Supported by:
This work was supported by the National Natural Science Foundation of China (21373206, 21202163, 21303194, 21476227, 21503219).

Abstract

Abstract:

Au and Au-containing bimetallic nanoparticles are promising catalysts for the green synthesis of fine chemicals. Here, we used a Au₆Pd/resin catalyst for the aerobic C-C cross-coupling of primary and secondary alcohols to produce higher ketones under mild conditions. This is of importance to the construction of a C-C bond. Various substrates were used in the reaction system, and moderate to good yields were obtained. The catalysts can be reused at least five times without decrease of yield. The control experiment and XAFS characterization results showed that hydrogen auto-transfer occurred on metallic Pd sites even under oxidative conditions. On alloying with Au, the Pd sites became resistant to oxidation and readily abstracted the β-H of the alcohols and transferred the hydride to the C=C bond in the reaction intermediate to give the saturated product.

Key words: Au-Pd alloys, C-C coupling reaction, Oxidation of alcohols, Hydrogen auto-transfer, Oxidation-resistant

Maoxiang Zhou, Leilei Zhang, Jeffrey T. Miller, Xiaofeng Yang, Xiaoyan Liu, Aiqin Wang, Tao Zhang. Hydrogen auto-transfer under aerobic oxidative conditions: Efficient synthesis of saturated ketones by aerobic C-C cross-coupling of primary and secondary alcohols catalyzed by a Au₆Pd/resin catalyst[J]. Chinese Journal of Catalysis, 2016, 37(10): 1764-1770.

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Hydrogen auto-transfer under aerobic oxidative conditions: Efficient synthesis of saturated ketones by aerobic C-C cross-coupling of primary and secondary alcohols catalyzed by a Au₆Pd/resin catalyst

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