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1 article(s) from Kumar, Nivesh

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds

Nivesh Kumar,
Santanu Ghosh,
Subhajit Bhunia and
Alakesh Bisai

Beilstein J. Org. Chem. 2016, 12, 1153–1169, doi:10.3762/bjoc.12.111

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Scheme 1: Synthesis of 2-oxindoles via oxidative processes.

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Figure 1: Substrates scope of one-pot ‘transition-metal-free’ IDC. The syntheses of compounds 4a–s according ...

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Figure 2: Further substrates scope of one-pot ‘transition metal-free’ IDC. Conditions A: KOt-Bu, iodine; cond...

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Figure 3: Substrates scope of ‘transition-metal-free’ IDC using KOt-Bu/I₂. Reproduced from [46].

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

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Figure 5: Substrates scope of ‘transition-metal-free’ IDC of C-alkylated anilides using DBU/I₂.

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Scheme 2: Oxidative coupling of C-arylated anilides (±)-11a–d. The synthesis of 12b as per method A has been ...

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Scheme 3: Synthesis of spirocyclic product through IDC The synthesis of 14 as per method A has been reproduce...

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Scheme 4: Dimerization of β-N-aryl-amidoesters 3a and b. Reproduced from [46].

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Scheme 5: Synthesis of dimeric 2-oxindoles utilizing IDC. The syntheses of 19a and b have been reproduced fro...

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Scheme 6: Plausible mechanism of ‘transition-metal-free’ IDC The mechanistic consideration in Scheme 6 has been repro...

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Scheme 7: Intramolecular-dehydrogenative-coupling (IDC) of 3a and 5a. Reproduced from [46].

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Scheme 8: IDC of 3a and 5a using different oxidants. Reproduced from [46].

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Scheme 9: Synthesis of 3-substituted-2-oxindoles from benzyl esters.

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Scheme 10: 3-Substituted-2-oxindoles from p-methoxybenzyl esters.

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Scheme 11: Synthetic elaboration using Tsuji–Trost reactions. Reproduced from [46].

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Published 08 Jun 2016

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Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds