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. 2019 Aug 2;21(15):5784-5788.
doi: 10.1021/acs.orglett.9b01482. Epub 2019 Jul 16.

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

Muthu Karuppasamy  1 , B S Vachan  1 , Perumal Vinoth  1 , Isravel Muthukrishnan  1 , Subbiah Nagarajan  2 , Laura Ielo  3 , Vittorio Pace  3 , Subrata Banik  4 , C Uma Maheswari  1 , Vellaisamy Sridharan  1   4
Affiliations

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

Muthu Karuppasamy et al. Org Lett. .

Abstract

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.

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