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Strategic Approach on N ‐Oxides in Gold Catalysis – A Case Study
Author(s) -
Schießl Jasmin,
Stein Philipp M.,
Stirn Judith,
Emler Kirsten,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801007
Subject(s) - chemistry , catalysis , pyridine , oxidative addition , kinetic energy , combinatorial chemistry , spectroscopy , organic chemistry , physics , quantum mechanics
An extensive kinetic study of selected key reactions of (oxidative) gold catalysis concentrates on the decrease of the catalytic activity due to inhibition of the gold(I) catalyst caused by pyridine derivatives that are obtained as by‐products if N ‐oxides are applied as oxygen donors. The choice of the examined pyridine derivatives and their corresponding N ‐oxides has been made regardless of their commercial availability; particular attention has been paid to the practical benefit which up to now has been neglected in most of the reaction screenings. The test reactions were monitored by GC and 1 H NMR spectroscopy. The received reaction constants provide information concerning a correlation between the electronic structure of the heterocycle and the catalytic activity. Based on the collected kinetic data, it was possible to develop a basic set of three N ‐oxides which have to be taken into account in further oxidative gold(I)‐catalyzed reactions.