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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.


C-Alkylation of anilides using KOt-Bu.
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Figure 4: C-Alkylation of anilides using KOt-Bu.

Mentions: With this result in hand, we thought of exploring IDC using C-alkylated substrates 10. For this purpose, a variety of C-alkylated β-N-arylamidoallyl, methallyl, dimethylallyl, and geranyl esters 10 were synthesized in good yields as per Fig. 4. These substrates were then utilized in IDC-promoted by DBU/I2 and the results are summarized in Fig. 5. Interestingly, under this conditions, we can synthesize a variety of 2-oxindoles 8 in moderate to good yields.


Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp 2 C – H and sp 3 C – H bonds
C-Alkylation of anilides using KOt-Bu.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

Figure 4: C-Alkylation of anilides using KOt-Bu.
Mentions: With this result in hand, we thought of exploring IDC using C-alkylated substrates 10. For this purpose, a variety of C-alkylated β-N-arylamidoallyl, methallyl, dimethylallyl, and geranyl esters 10 were synthesized in good yields as per Fig. 4. These substrates were then utilized in IDC-promoted by DBU/I2 and the results are summarized in Fig. 5. Interestingly, under this conditions, we can synthesize a variety of 2-oxindoles 8 in moderate to good yields.

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.