- Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and SNAr Chemistry
-
A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious choice of simple and inexpensive additives.
- Polidano, Kurt,Reed-Berendt, Benjamin G.,Basset, Ana?s,Watson, Andrew J. A.,Williams, Jonathan M. J.,Morrill, Louis C.
-
supporting information
p. 6716 - 6719
(2017/12/26)
-
- Ruthenium-catalyzed transfer hydrogenation of amino- and amido-substituted acetophenones
-
The ruthenium-catalyzed transfer hydrogenation of electron-rich amino-substituted acetophenones is reported. Variation of the reductant, ligands, base, and solvent allowed reaction optimization. A key discovery was the use of 1,4-butanediol as an irreversible reducing agent, which significantly improved the conversion. A range of amino- and amido-substituted aryl ketones were explored, and they all gave the corresponding alcohols in good yield, which demonstrates the wider applicability of this process. The ruthenium-catalyzed reduction of electron-rich amino-substituted acetophenones with 1,4-butanediol as an irreversible reducing agent is reported. Optimization of the conditions and variation of the amino substituent are explored as is the use of amido- and sulfonamidoacetophenones with varying results. Copyright
- Watson, Andrew J. A.,Fairbanks, Antony J.
-
supporting information
p. 6784 - 6788
(2013/11/06)
-
- Cyclizations via enamine intermediates with amine dehydrogenations
-
The mercury-edta dehydrogenation of the 4'-aminosubstituted-acetophenones 1, 8a and 9a produced the ring cleavaged derivatives 7, 11a and 12a, while the piperidine and its derivatives 10a - 10e gave rise to tetracyclic compounds 16a - 16e and to methylenedi-enamines 19a - 19d, the additionally C-1-fragment in 19a - 19d probably coming from mercury edta. With addition of m-nitrobenzaldehyde to the mercury-edta dehydrogenation of substituted phenylpiperidines another route only generated the di-enamines 22.
- M?hrle,Mehrens
-
p. 214 - 224
(2007/10/03)
-