- Copper-catalyzed electrophilic amination of organozinc nucleophiles: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons
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This paper details new copper-catalyzed electrophilic amination reactions of diorganozinc reagents using O-benzoyl hydroxylamines as electrophilic nitrogen sources that may be accessed in one step. Simple and functionalized aryl, heteroaryl-, benzyl, n-alkyl, sec-alkyl, and tert-alkyl nucleophiles couple with R2NOC(O)Ph and RHNOC(O)Ph reagents in the presence of catalytic quantities of copper salts to provide tertiary and secondary amines, respectively, in generally good yields. In many cases, the product may be isolated analytically pure after a simple extractive workup. The amination process is shown to tolerate a significant degree of steric demand. The amination of nominally unreactive Caryl-H bonds via a sequential directed ortho metalation/transmetalation/catalytic amination reaction sequence is detailed. The direct Cu-catalyzed amination of Grignard reagents using cocatalysis by ZnCl2 is described.
- Herman, Ashley M.,Johnson, Jeffrey S.
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p. 219 - 224
(2007/10/03)
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- Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents
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(Chemical Equation Presented). The copper-catalyzed electrophilic amination of functionalized diarylzinc reagents with O-acyl hydroxylamines allows for the preparation of functionalized tertiary arylamines in high yields, and is noteworthy for the mild re
- Berman, Ashley M.,Johnson, Jeffrey S.
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p. 364 - 366
(2007/10/03)
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- High pressure organic chemistry; XI. A new convenient synthesis of aromatic amines from activated phenols
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Aryl triflates containing electron-withdrawing substituents efficiently react with amines in refluxing acetonitrile or at 10 kbar pressure to give various aromatic amines.
- Kotsuki,Kobayashi,Suenaga,Nishizawa
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p. 1145 - 1147
(2007/10/02)
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