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Your search keyword '"Aronica, Laura A."' showing total 4 results
Start Over Author "Aronica, Laura A." Topic oxygen heterocycles
4 results on '"Aronica, Laura A."'

2. Cyclocarbonylative Sonogashira Reactions of 1-Ethynylbenzyl Alcohols: Synthesis of 1-Carbonylmethylene-1,3-Dihydroisobenzofurans

Author

Aronica, Laura Antonella, Giannotti, Luca, Tuci, Giulia, and Zinna, Francesco

Subjects
Synthetic methods, Oxygen heterocycles, Cyclisation, Cross-coupling, Carbonylation, Homogeneous catalysis
Abstract

In this work, we present a carbonylative Sonogashira reaction of o-ethynyl benzyl alcohols and aryl iodides, followed by a cyclization process to selectively give carbonylmethylene isobenzofurans in high yields and in an atom-economic fashion. The reaction can be carried out in the absence of CuI, with a small amount of PdCl2(PPh3)(2) (0.2-0.5 mol-%), using aryl iodides bearing both electron-withdrawing and electron-donating groups. Of the two possible stereoisomeric products, Z-isobenzofuran derivatives were obtained as major products. But, when the reaction was extended to a secondary alcohol, an interesting switch in stereoselectivity was observed.

Published
2015
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4. Synthesis of Functionalised 3-Isochromanones by Silylcarbocyclisation/Desilylation Reactions.

Author

Albano, Gianluigi, Morelli, Martina, and Aronica, Laura Antonella

Subjects
CHROMANONES, RING formation (Chemistry), SILYLATION, CHEMICAL synthesis, BENZYL alcohol
Abstract

A new protocol for the synthesis of 3-isochromanone derivatives based on rhodium-promoted silylcarbocyclisation reactions of ethynylbenzyl alcohol with different arylsilanes is described. The structure of the isochromanone depends upon the reaction conditions used: when the reaction is carried out without base, ( Z)-4-[(aryldimethylsilyl)methylene]isochroman-3-ones are obtained as major products. These compounds can be submitted to a desilylation/aryl migration reaction to give 4-(arylmethyl)isochroman-3-ones in high yields. In contrast, in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), hydrogenation of methyleneisochroman-3-ones takes place, and the corresponding β-(silylmethyl)-3-isochromanones are formed. Moreover, when internal alkynes are treated with hydrosilanes under silylcarbocyclisation reaction conditions, alcoholysis of the hydrosilanes occurs exclusively. [ABSTRACT FROM AUTHOR]

Published
2017
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