Ruthenium catalyzed β-C(sp3)-H functionalization on the 'privileged' piperazine nucleus

V Murugesh; Christian Bruneau; Mathieu Achard; Apurba Ranjan Sahoo; Gangavaram V M Sharma; Surisetti Suresh

doi:10.1039/c7cc05604d

Ruthenium catalyzed β-C(sp³)-H functionalization on the 'privileged' piperazine nucleus

Chem Commun (Camb). 2017 Sep 19;53(75):10448-10451. doi: 10.1039/c7cc05604d.

Authors

V Murugesh¹, Christian Bruneau², Mathieu Achard², Apurba Ranjan Sahoo², Gangavaram V M Sharma³, Surisetti Suresh¹

Affiliations

¹ Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India. surisetti@iict.res.in suresh.surisetti@yahoo.in and Academy of Scientific and Innovative Research (AcSIR), CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India.
² UMR6226, Institut des Sciences Chimiques de Rennes, Université de Rennes1, Organometallics: Materials and Catalysis, Campus de Beaulieu, 35042 Rennes Cedex, France.
³ Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500 007, India. surisetti@iict.res.in suresh.surisetti@yahoo.in.

PMID: 28884776
DOI: 10.1039/c7cc05604d

Abstract

β-C(sp³)-H functionalization on the 'privileged' piperazine nucleus has been disclosed using ruthenium catalysis. The ruthenium catalyzed synthesis of a variety of piperazine fused indoles from ortho-piperazinyl (hetero)aryl aldehydes is presented. This transformation takes place via the dehydrogenation of piperazine followed by an intramolecular nucleophilic addition of the transient enamine moiety onto the carbonyl group and aromatization cascade.