Direct Access to 9‑Chloro‑1H‑benzo[b]furo[3,4‑e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2‑C–H Bond Activation Cascade

An efficient Pd­(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo­[b]­furo­[3,4-e]­azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladat...

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Bibliographic Details
Published in:Organic letters 2019-08, Vol.21 (15), p.5784-5788
Main Authors: Karuppasamy, Muthu, Vachan, B. S, Vinoth, Perumal, Muthukrishnan, Isravel, Nagarajan, Subbiah, Ielo, Laura, Pace, Vittorio, Banik, Subrata, Maheswari, C. Uma, Sridharan, Vellaisamy
Format: Article
Language:English
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Summary:An efficient Pd­(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo­[b]­furo­[3,4-e]­azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C–Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01482