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. ©
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 / Karuppasamy, M.; Vachan, B. S.; Vinoth, P.; Muthukrishnan, I.; Nagarajan, S.; Ielo, L.; Pace, V.; Banik, S.; Maheswari, C. U.; Sridharan, V.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 21:15(2019), pp. 5784-5788. [10.1021/acs.orglett.9b01482]
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
Pace V.;
2019
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. ©I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
