Reductive C(sp2)-N Elimination from Isolated Pd(IV) Amido Aryl Complexes Prepared Using H2O2 as Oxidant

Elikplim Abada; Peter Y Zavalij; Andrei N Vedernikov

doi:10.1021/jacs.6b12648

Reductive C(sp²)-N Elimination from Isolated Pd(IV) Amido Aryl Complexes Prepared Using H₂O₂ as Oxidant

J Am Chem Soc. 2017 Jan 18;139(2):643-646. doi: 10.1021/jacs.6b12648. Epub 2017 Jan 5.

Authors

Elikplim Abada¹, Peter Y Zavalij¹, Andrei N Vedernikov¹

Affiliation

¹ Department of Chemistry and Biochemistry, University of Maryland , College Park, Maryland 20742, United States.

PMID: 28048934
DOI: 10.1021/jacs.6b12648

Abstract

Di-2-pyridyl ketone (dpk)-supported amidoarylpallada(II)cycles derived from various 2-(N-R-amino)biphenyls (R = H, Me, CF₃CO, MeSO₂, CF₃SO₂) react with hydrogen peroxide in MeOH, THF, MeCN or AcOH to form the corresponding C-N coupled products, N-R-substituted carbazoles, in 82-98% yield. For R = MeSO₂ and CF₃SO₂, the corresponding reaction intermediates, amidoaryl Pd(IV) complexes were isolated and characterized by single crystal X-ray diffraction and/or NMR spectroscopy. For the first time, the C(sp²)-N reductive elimination from isolated amidoaryl Pd(IV) complexes has been studied in detail.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't