Lewis Acid Directed Regioselective Metalations of Pyridazine

Moritz Balkenhohl; Harish Jangra; Tobias Lenz; Marian Ebeling; Hendrik Zipse; Konstantin Karaghiosoff; Paul Knochel

doi:10.1002/anie.201903839

Lewis Acid Directed Regioselective Metalations of Pyridazine

Angew Chem Int Ed Engl. 2019 Jul 1;58(27):9244-9247. doi: 10.1002/anie.201903839. Epub 2019 May 24.

Authors

Moritz Balkenhohl¹, Harish Jangra¹, Tobias Lenz¹, Marian Ebeling¹, Hendrik Zipse¹, Konstantin Karaghiosoff¹, Paul Knochel¹

Affiliation

¹ Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstrasse 5-13, Haus F, 81377, München, Germany.

PMID: 31034125
DOI: 10.1002/anie.201903839

Abstract

Mono- or bidentate boron Lewis acids trigger a regioselective magnesiation or zincation of pyridazine in position C3 (ortho product) or C4 (meta product). The regioselectivity of the metalation was rationalized with the help of calculated pK_a values of both pyridazine and pyridazine/Lewis acid complexes.

Keywords: TMP bases; frustrated Lewis pairs; magnesiation; pyridazine; zincation.

Publication types

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