Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)

Mercedes K. Taylor; Martin Juhl; Gul Barg Hadaf; Dasol Hwang; Ever Velasquez; Julia Oktawiec; Jonathan B. Lefton; Tomče Runčevski; Jeffrey R. Long; Ji-Woong Lee

doi:10.1039/C9CC08614E

Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)†

Mercedes K. Taylor,

^abc Martin Juhl,^d Gul Barg Hadaf,^d Dasol Hwang,^d Ever Velasquez,^ce Julia Oktawiec,^b Jonathan B. Lefton,^f Tomče Runčevski,^f Jeffrey R. Long

*^bce and Ji-Woong Lee

*^d

Author affiliations

* Corresponding authors

^a Center for Integrated Nanotechnologies, Sandia National Laboratories, Albuquerque, New Mexico 87185, USA

^b Department of Chemistry, University of California, Berkeley, California 94720, USA
E-mail: jrlong@berkeley.edu

^c Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA

^d Department of Chemistry & Nano-Science Center, University of Copenhagen, Copenhagen 2100, Denmark
E-mail: jiwoong.lee@chem.ku.dk

^e Department of Chemical and Biomolecular Engineering, University of California, Berkeley, California 94720, USA

^f Department of Chemistry, Southern Methodist University, Texas 75205, USA

Abstract

A facile route to 4,4′-bipyrazole (H₂bpz) and other symmetric bipyrazoles is achieved via the palladium-catalyzed homocoupling of a pyrazole boronic ester in the presence of air and water, enabling us to provide the first crystal structures and evidence of structural phase changes in the bipyrazolate-based metal–organic framework Co(bpz).

This article is part of the themed collection: Chemical Communications HOT Articles

Chemical Communications

Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)†

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Palladium-catalyzed oxidative homocoupling of pyrazole boronic esters to access versatile bipyrazoles and the flexible metal–organic framework Co(4,4′-bipyrazolate)

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