Journal
SCIENCE
Volume 343, Issue 6173, Pages 853-857Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1248042
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Funding
- NSF [CHE-1213409]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1213409] Funding Source: National Science Foundation
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Regioselective C-H functionalization of arenes has widespread applications in synthetic chemistry. The regioselectivity of these reactions is often controlled by directing groups or steric hindrance ortho to a potential reaction site. Here, we report a catalytic intermolecular C-H silylation of unactivated arenes that manifests very high regioselectivity through steric effects of substituents meta to a potential site of reactivity. The silyl moiety can be further functionalized under mild conditions but is also inert toward many common organic transformations, rendering the silylarene products useful building blocks. The remote steric effect that we observe results from the steric properties of both the rhodium catalyst and the silane.
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