Journal
NATURE CHEMISTRY
Volume 7, Issue 10, Pages 829-834Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2326
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Funding
- Cancer Prevention Research Institute of Texas [R1118]
- Welch Foundation [F-1781]
- Frasch Foundation
- American Chemical Society Petroleum Research Fund
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Site-selective C-H functionalization has emerged as an attractive tool for derivatizing complex synthetic intermediates, but its use for late-stage diversification is limited by the functional groups that can be introduced, especially at unactivated sp(3)-hybridized positions. To overcome this, we introduce a strategy that directly installs a sulfonyloxy group at a beta-C-H bond of a masked alcohol and subsequently employs nucleophilic substitution reactions to prepare various derivatives. Hydroxyl groups are widely found in bioactive molecules and are thus readily available as synthetic handles. A directing group is easily added (and subsequently removed) from the alcohols such that a formal site-selective beta-C-H sulfonyloxylation of these alcohols is achieved. Substitution reactions with carbon, nitrogen, oxygen and other nucleophiles then lead to diverse functionalizations that may help to streamline the synthesis of complex analogues for drug discovery.
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