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A C(sp2)−H Dehydrogenation of Heteroarenes and Arenes by a Functionalized Aluminum Hydride.
- Source :
- Chemistry - A European Journal; 10/4/2017, Vol. 23 Issue 55, p13633-13637, 5p
- Publication Year :
- 2017
-
Abstract
- The 2-aminophenylaluminum dihydride (2-TMP-C<subscript>6</subscript>H<subscript>4</subscript>)AlH<subscript>2</subscript> ( 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<superscript>2</superscript>)−H dehydroalumination to aluminum heteroaryls ( 3 and 4). Moreover, 2 reacted with PhCCSiMe<subscript>3</subscript> (at room temperature) and Ph<subscript>2</subscript>CCNR (R= iPr or 2,6- iPr<subscript>2</subscript>C<subscript>6</subscript>H<subscript>3</subscript>, 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<superscript>2</superscript>)−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<superscript>2</superscript>)−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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 23
- Issue :
- 55
- Database :
- Complementary Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 125485333
- Full Text :
- https://doi.org/10.1002/chem.201703804