A Metal‐Free Oxidative Dehydrogenative Diels–Alder Reaction for Selective Functionalization of Alkylbenzenes. Issue 32 (19th May 2017)

• Record Type: Journal Article
• Authors: Manna, Srimanta; Antonchick, Andrey P.
• Is Part Of: Chemistry. Volume 23:Issue 32(2017)
• Page Start: 7825
• Page End: 7829
• Publication Date: 2017-05-19
• Subjects: C−H activation -- cycloaddition -- dehydrogenative coupling -- metal-free synthesis -- oxidative coupling; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201701535
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Functionalization of C(sp 3 )−H bonds under metal‐free reaction conditions is a great challenge due to poor bond reactivity. A novel metal‐free oxidative dehydrogenative Diels–Alder reaction of alkylbenzene derivatives with alkenes through C(sp 3 )−H bond functionalization is described. The developed oxidative method provides a straightforward approach to biologically relevant 1, 4‐phenanthraquinone and isoindole derivatives from readily available starting materials. Furthermore, the synthesis of nitrostyrenes from enylbenzene derivatives by selective C(sp 3 )−H bond functionalization has been demonstrated. Abstract : Linking rings : A metal‐free oxidative dehydrogenative Diels–Alder reaction of alkylbenzene derivatives with alkenes was developed. The direct functionalization of C(sp 3 )−H bonds of alkylbenzenes provides access to naphthalene derivatives. The broad reaction scope and application of various functional groups was shown. Furthermore, direct transformation of ethylbenzenes to nitrostyrenes was demonstrated.