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Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp 2 C – H and sp 3 C – H bonds

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ABSTRACT

The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a ‘transition-metal-free’ intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon–carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.

No MeSH data available.


Synthesis of 3-substituted-2-oxindoles from benzyl esters.
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C9: Synthesis of 3-substituted-2-oxindoles from benzyl esters.

Mentions: Shifting our attention towards the synthetic application of our IDC methodology, we put forward our effort towards the synthesis of 3-alkylated or arylated 2-oxindoles. Towards this, we subjected to react, the oxidative coupling products (±)-6, (±)-12c and d having benzyl (Bn) or p-methoxybenzyl (PMB) esters with a catalytic amount of Pd on activated charcoal (10% Pd on charcoal) under atmospheric pressure of hydrogen gas in MeOH/EtOH (Scheme 9).


Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp 2 C – H and sp 3 C – H bonds
Synthesis of 3-substituted-2-oxindoles from benzyl esters.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979638&req=5

C9: Synthesis of 3-substituted-2-oxindoles from benzyl esters.
Mentions: Shifting our attention towards the synthetic application of our IDC methodology, we put forward our effort towards the synthesis of 3-alkylated or arylated 2-oxindoles. Towards this, we subjected to react, the oxidative coupling products (±)-6, (±)-12c and d having benzyl (Bn) or p-methoxybenzyl (PMB) esters with a catalytic amount of Pd on activated charcoal (10% Pd on charcoal) under atmospheric pressure of hydrogen gas in MeOH/EtOH (Scheme 9).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a ‘transition-metal-free’ intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon–carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.

No MeSH data available.