Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 11, Pages 7872-7880Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00781
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- University Nursing Program for Young Scholars with Creative Talents in Heilongjiang Province [UNPYSCT-2017124]
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In this study, a new method was developed to enhance the coordination of Pd catalysts with weak-coordinating substrates using a commercially available sulfonic acid, enabling arylation and alkenylation of C(sp(3))-H bonds of Weinreb amides.
Pd-catalyzed modification of C-H bonds via chelation with weakly coordinating groups normally requires a transient directing group or presynthesized nitrogen-based strong coordinating ligands. Herein, we report Pd(II)-catalyzed C(sp(3))-H arylation and alkenylation of Weinreb amides. A commercially available, inexpensive sulfonic acid was employed to enhance the coordination of the catalyst with weak-coordinating substrates by increasing the electrophilicity of in situ formed palladium catalysts.
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