Synlett 2017; 28(13): 1548-1553
DOI: 10.1055/s-0036-1588761
cluster
© Georg Thieme Verlag Stuttgart · New York

Development of 3,5-Di-tert-butylphenol as a Model Substrate for Biomimetic Aerobic Copper Catalysis

Ohhyeon Kwon
a   Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: jean-philip.lumb@mcgill.ca
,
Kenneth Virgel N. Esguerra
a   Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: jean-philip.lumb@mcgill.ca
,
Michael Glazerman †
b   Department of Chemistry and Biochemistry, Concordia University, 7141 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: dr.x@concordia.ca
,
Laurène Petitjean
a   Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: jean-philip.lumb@mcgill.ca
,
Yalun Xu
a   Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: jean-philip.lumb@mcgill.ca
,
Xavier Ottenwaelder
b   Department of Chemistry and Biochemistry, Concordia University, 7141 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: dr.x@concordia.ca
,
a   Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 0B8, Canada   eMail: jean-philip.lumb@mcgill.ca
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 17. Januar 2017

Accepted after revision: 28. Februar 2017

Publikationsdatum:
28. März 2017 (online)


In memoriam

Abstract

We develop 3,5-di-tert­butylphenol as a strategic substrate for the evaluation of biomimetic Cu2–O2 complexes intended to mimic the activity of tyrosinase. We describe a practical and scalable synthesis and validate its use in an aerobic ortho-oxygenation catalyzed by N,N′-di-tert-butylethylenediamine and [Cu(CH3CN)4]PF6.

Supporting Information