Diisobutylaluminum Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles.

Title Diisobutylaluminum Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles.
Authors H. Kinoshita; A. Ueda; H. Fukumoto; K. Miura
Journal Org Lett
DOI 10.1021/acs.orglett.7b00038
Abstract

An efficient method for preparing unsymmetrically multisubstituted siloles is described. The reaction of 1-hydrosilyl-4-silyl-1,3-enynes with diisobutylaluminum hydride (DIBAL-H) gave multisubstituted siloles in good to high yields. This method could be applied to the synthesis of benzosiloles using 2-hydrosilyl-1-(silylethynyl)benzenes as substrates. The silole formation was also promoted even by a substoichiometric amount of DIBAL-H. The reaction provides a straightforward method to prepare siloles and benzosiloles.

Citation H. Kinoshita; A. Ueda; H. Fukumoto; K. Miura.Diisobutylaluminum Hydride Promoted Cyclization of 1-Hydrosilyl-4-silyl-1,3-enynes to Polysubstituted Siloles.. Org Lett. 2017. doi:10.1021/acs.orglett.7b00038

Related Elements

Aluminum

See more Aluminum products. Aluminum (or Aluminium) (atomic symbol: Al, atomic number: 13) is a Block P, Group 13, Period 3 element with an atomic weight of 26.9815386. It is the third most abundant element in the earth's crust and the most abundant metallic element. Aluminum Bohr Model Aluminum's name is derived from alumina, the mineral from which Sir Humphrey Davy attempted to refine it from in 1812. Aluminum was first predicted by Antoine Lavoisier 1787 and first isolated by Hans Christian Øersted in 1825. Aluminum is a silvery gray metal that possesses many desirable characteristics. It is light, nonmagnetic and non-sparking. It stands second among metals in the scale of malleability, and sixth in ductility. It is extensively used in many industrial applications where a strong, light, easily constructed material is needed. Elemental AluminumAlthough it has only 60% of the electrical conductivity of copper, it is used in electrical transmission lines because of its light weight. Pure aluminum is soft and lacks strength, but alloyed with small amounts of copper, magnesium, silicon, manganese, or other elements, it imparts a variety of useful properties.

Related Forms & Applications