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Chem Soc Rev. 2016 Feb 7;45(3):506-16. doi: 10.1039/c5cs00821b.

Gold-catalyzed transformations of α-diazocarbonyl compounds: selectivity and diversity.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. lliu@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn.
2
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. lliu@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.

Abstract

Metal carbenes, generated from the decomposition of diazo compounds by transition-metals, have a broad range of applications in organic synthesis. The progress of organic transformation via transition metal (such as Rh, Cu, Fe, Ag) carbenes has been well summarized in a few excellent reviews. This review will summarize gold-catalyzed transformations of α-diazocarbonyl compounds by highlighting the specificity and applicability of these diverse transformations such as X-H insertion, C-H functionalization, cyclopropanation, cycloaddition, and coupling reactions. In order to understand these reactions, the mechanistic rationale for selected examples is also provided.

PMID:
26658761
DOI:
10.1039/c5cs00821b

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