Abstract
A general and efficient iron‐catalyzed C‐alkylation of oxindoles has been developed. This borrowing hydrogen approach employing a (cyclopentadienone)iron carbonyl complex (2 mol %) exhibited a broad reaction scope, allowing benzylic and simple primary and secondary aliphatic alcohols to be employed as alkylating agents. A variety of oxindoles underwent selective mono‐C3‐alkylation in good‐to‐excellent isolated yields (28 examples, 50–92 % yield, 79 % average yield).
Highlights
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Oxindoles that are mono- or disubstituted at the C3 position are commonly employed in drug discovery programs,[2] with examples including the development of HIV-1 non-nucleoside reverse transcriptase inhibitors, spirocyclic compounds with anti-cancer and anti-inflammatory properties, and antagonists of progesterone and 5hydroxytryptamine7 (5-HT7) receptors (Scheme 1 A)
An alternative approach employs the borrowing hydrogen (BH) principle, known as hydrogen autotransfer, which allows bench-stable and inexpensive alcohols to be used as alkylating agents, generating water as the sole byproduct.[4]
Summary
Please note: Changes made as a result of publishing processes such as copy-editing, formatting and page numbers may not be reflected in this version. Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols
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