Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 21, Pages 8309-8313Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9015369
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Funding
- Welch Foundation [E-1571]
- NIGMS [R01GM077635]
- A.P.Sloan Foundation
- Camille and Henry Dreyfus Foundation
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A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene Pentafluorobenzene, benzothiazole,and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive.
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