Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis

Autor:	Valentina Beghetto, Matteo Bertoldini, Alberto Scrivanti, Ugo Matteoli
Rok vydání:	2008
Předmět:	chemistry.chemical_classification Base (chemistry) Organic Chemistry Alcohol Biochemistry Medicinal chemistry Methylenedioxy Catalysis Reaction rate chemistry.chemical_compound chemistry Drug Discovery Organic chemistry Chemoselectivity Benzene
Zdroj:	Tetrahedron. 64:543-548
ISSN:	0040-4020
DOI:	10.1016/j.tet.2007.11.019
Popis:	Pd(OAc) 2 in combination with P( t -Bu) 3 catalyzes the coupling of β-methallyl alcohol with 1-bromo-3,4-(methylenedioxy)benzene ( 1a ), 1-bromo-4-methoxybenzene ( 1b ), or 1-bromo-4- tert -butylbenzene ( 1c ). The reaction affords the corresponding 2-methyl-3-aryl-propanals, which are valuable floral fragrances. With 1a or 1b high reaction rates are obtained at 130 °C using NMP/water mixtures and an inorganic base such as Na 2 CO 3 . The chemoselectivity of the reaction is almost complete, so that the process appears practically feasible. In contrast, the coupling of β-methallyl alcohol with 1c proceeds with low reaction rates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::5e9b8452f94d2be0e6335d37dfc6adc4 https://doi.org/10.1016/j.tet.2007.11.019 Zobrazit plný text záznamu Full Text from ScienceDirect