Tailored quinones support high-turnover Pd catalysts for oxidative C–H arylation with O 2
Author(s) -
Chase A. Salazar,
Kaylin N. Flesch,
Brandon E. Haines,
Philip S. Zhou,
Djamaladdin G. Musaev,
Shan S. Stahl
Publication year - 2020
Publication title -
science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 12.556
H-Index - 1186
eISSN - 1095-9203
pISSN - 0036-8075
DOI - 10.1126/science.abd1085
Subject(s) - catalysis , quinone , chemistry , palladium , carbon fibers , oxygen , oxidative coupling of methane , photochemistry , oxidative phosphorylation , redox , combinatorial chemistry , organic chemistry , materials science , composite number , composite material , biochemistry
A subtle balancing act for quinones Palladium catalysis is widely used in drug synthesis to form carbon-carbon bonds, but typically both carbon centers need to be activated ahead of time. Although introducing oxygen as an oxidant diminishes the need for preactivation, the catalysis then tends to be less efficient, especially in the case of arene coupling. Salazaret al. pinpointed the role of quinone co-catalysts in these processes and determined that after accelerating carbon-carbon bond formation, the quinone slows down catalyst reoxidation by oxygen. Appending bulky substituents to the quinone struck a better balance and substantially enhanced catalytic efficiency.Science , this issue p.1454
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