A C(sp(2) )-H Dehydrogenation of Heteroarenes and Arenes by a Functionalized Aluminum Hydride.

Title A C(sp(2) )-H Dehydrogenation of Heteroarenes and Arenes by a Functionalized Aluminum Hydride.
Authors S. Chen; B. Li; X. Wang; Y. Huang; J. Li; H. Zhu; L. Zhao; G. Frenking; H.W. Roesky
Journal Chemistry
DOI 10.1002/chem.201703804
Abstract

The 2-aminophenylaluminum dihydride (2-TMP-C6 H4 )AlH2 ?(2) has been prepared and characterized for the first time. Compound?2 features an intramolecular N???Al donor-acceptor bond. 2 reacted with N-methylpyrrole and N-methylindole (both at 50?°C) by means of the elusive AlH C(sp(2) )-H dehydroalumination to aluminum heteroaryls?(3 and 4). Moreover, 2 reacted with PhCCSiMe3 (at room temperature) and Ph2 CCNR (R=iPr or 2,6-iPr2 C6 H3 , at -30 to 20?°C ) to yield aluminaindene heterocycle?(8) and alumina-aza-naphthalene heterocycle?(9 and 10), respectively. These reactions underwent hydroalumination followed by AlH C(sp(2) )-H dehydroalumination. The reaction mechanism has been studied by combining experiment and quantum chemical calculations, with the result that the key heteroarene or arene C(sp(2) )-H bond activation is involved under cooperative interaction by the inherent N/Al donor/acceptor pair. The reported reactions open a straightforward route to heteroaryl and unique heterocyclic aluminum compounds.

Citation S. Chen; B. Li; X. Wang; Y. Huang; J. Li; H. Zhu; L. Zhao; G. Frenking; H.W. Roesky.A C(sp(2) )-H Dehydrogenation of Heteroarenes and Arenes by a Functionalized Aluminum Hydride.. Chemistry. 2017;23(55):1363313637. doi:10.1002/chem.201703804

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.

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