- Palladium-Catalyzed Desulfitative Oxidative Coupling between Arenesulfinic Acid Salts and Allylic Alcohols: A Strategy for the Selective Construction of β-Aryl Ketones and Aldehydes
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An efficient palladium-catalyzed desulfitative oxidative coupling of sodium arylsulfinites for highly region-selective Heck-type reaction of allylic alcohols has been developed. The compatibility of the functionalities of -I, -Br, and -F would explore further postfunctionalization of the C-X bonds. This method provides a new and straightforward protocol for the synthesis of β-aryl ketones and aldehydes. The deuterium labeling experiments indicated that this transformation may proceed via a [1, 2-H] shift process.
- Liao, Jianhua,Zhang, Zhenming,Tang, Xiaodong,Wu, Wanqing,Guo, Wei,Jiang, Huanfeng
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p. 8903 - 8909
(2015/09/15)
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- Replacing a stoichiometric silver oxidant with air: Ligated Pd(II)-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity
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Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(II)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important β-aryl carbonyl derivatives. This green approach, which didn't require acid or base, allowed the compatibility of a range of functionalities (inclusive of -I, -Br & -Cl), resulting in the construction of structurally-diverse dihydrochalcones, α-benzyl-α′-alkyl acetones, α-benzyl β-keto esters and dihydrocinnamaldehydes. In addition to organoboronic acids, efficient coupling was also achieved with boronic esters and trifluoroborate salts. A deuterium labelling experiment revealed an interesting 1,2-hydrogen shift after β-arylation in the catalytic process. the Partner Organisations 2014.
- Vellakkaran, Mari,Andappan, Murugaiah M.S.,Kommu, Nagaiah
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supporting information
p. 2788 - 2797
(2014/05/06)
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