Synthesis of 4-Vinylbiphenyl Derivatives by Pd(II)-1,2-Diamino-cyclohexane Complex Catalyzed Suzuki-Miyaura Reaction

Liu, Y.; Ma, Xiaochu; Liu, P.; Xie, Jia; Dai, Baifan

doi:10.14233/ajchem.2014.16972

Cited by 1 publication

(1 citation statement)

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“…Unless otherwise noted, all reactants or reagents including dry solvents were obtained from commercial suppliers and used as received. Malonate 2a , 30 2b , 31 2c , 32 2d , 33 2f , 3h styrene 1i , 34 1k , 35 1l , 36 and 1-cyclopropyl-1-phenylethyrene 37 were prepared according to the procedure reported.…”

Section: Methodsmentioning

confidence: 99%

trans-Diastereoselective Syntheses of γ-Lactones by Visible Light-Iodine-Mediated Carboesterification of Alkenes

2019

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This study aims to develop an intermolecular lactonization reaction of alkenes with carbonyls mediated by visible light and molecular iodine. The one-step reaction involved the carboesterification of alkenes to produce the corresponding lactones in moderate to good yield. It was also revealed that it is possible to control the diastereoselectivity of the reaction by altering the base used and the reaction conditions. When water was added as a solvent, the reaction resulted in the formation of lactones with trans-selectivity. A mechanistic investigation was undertaken and it was found that the reaction requires the generation of an iodine radical from molecular iodine, driven by visible light irradiation, and proceeds via the formation of an iodine radical alkene adduct. The proposed reaction is an example of a rare-metal free intermolecular addition cyclization reaction, which is an environment-friendly chemical process that only uses molecular iodine. In addition, since diastereoselectivity was observed without the use of any specific reagents, the developed methodology is an example of a novel stereoselective transformation using only cost-effective reagents.

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