- Platinum-Catalyzed, Terminal-Selective C(sp3)-H Oxidation of Aliphatic Amines
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This Communication describes the terminal-selective, Pt-catalyzed C(sp3)-H oxidation of aliphatic amines without the requirement for directing groups. CuCl2 is employed as a stoichiometric oxidant, and the reactions proceed in high yield at Pt loadings as low as 1 mol%. These transformations are conducted in the presence of sulfuric acid, which reacts with the amine substrates in situ to form ammonium salts. We propose that protonation of the amine serves at least three important roles: (i) it renders the substrates soluble in the aqueous reaction medium; (ii) it limits binding of the amine nitrogen to Pt or Cu; and (iii) it electronically deactivates the C-H bonds proximal to the nitrogen center. We demonstrate that this strategy is effective for the terminal-selective C(sp3)-H oxidation of a variety of primary, secondary, and tertiary amines.
- Lee, Melissa,Sanford, Melanie S.
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supporting information
p. 12796 - 12799
(2015/10/28)
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- N-t-butoxycarbonyl protection of primary and secondary amines in the hydroboration reaction: Synthesis of amino alcohols
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The use of the BOC group as a protecting group in the hydroboration of aminoalkenes is described. The isolated yields of amino alcohols via the hydroboration-oxidation sequence are excellent.
- Kabalka,Li,Pace
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p. 2135 - 2143
(2007/10/02)
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- Mild LIBF4-Promoted Aminolysis of Oxetanes
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LiBF4 in acetonitrile efficiently catalyzes the aminolysis of trimethylene oxide and 2-octyl oxetane under mild conditions (r.t. or 80 deg C) to give the corresponding γ-amino alcohols in very good yields.
- Chini, Marco,Crotti, Paolo,Favero, Lucilla,Macchia, Franco
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p. 761 - 764
(2007/10/02)
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- The Conformational Analysis of Saturated Heterocycles. Part 100. 1-Oxa-3-azacyclohexanes
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Conformational equilibria and barriers to ring and nitrogen inversion are determined by 1H and 13C n.m.r. for 13 1-oxa-3-azacyclohexanes and correlated with recent work on the conformational analysis of saturated heterocycles.
- Katritzky, Alan R.,Baker, Victor J.,Brito-Palma, Fernando M. S.
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p. 1739 - 1745
(2007/10/02)
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