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2005
Boration
O 0277
14- 055
Regiospecific Functionalization of Methyl C—H Bonds of Alkyl Groups in Reagents with Heteroatom Functionality. — Alkanes containing ether, acetal, amino or
fluoro functionalities undergo selective borylation at the least hindered and least electron-rich methyl group to give the terminal alkylboronate esters (III). High yields are
obtained when the organic substrate is present in excess (substrate:diborane = 10:1).
The reactions occurred preferentially at the methyl group closer to the heteroatom as
shown in the reaction of (IV) or by competition experiments with (Ib) and (VII). The
products from the borylation reactions can be converted directly to alkylarenes, alkyltrifluoroborates or alcohols such as (X), (XII) or (XIII). — (LAWRENCE, J. D.;
TAKAHASHI, M.; BAE, C.; HARTWIG*, J. F.; J. Am. Chem. Soc. 126 (2004) 47,
15334-15335; Dep. Chem., Yale Univ., New Haven, CT 06520, USA; Eng.) —
Kieslich
2005
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