Journal
ORGANIC LETTERS
Volume 21, Issue 2, Pages 540-544Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03871
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Funding
- Shanghai Institute of Materia Medica
- Shanghai Institute of Organic Chemistry
- Chinese Academy of Sciences
- NSFC [21472211, 21502212, 21772211]
- Youth Innovation Promotion Association CAS [2014229, 2018293]
- Institutes for Drug Discovery and Development, the Chinese Academy of Sciences [CASIMM0120163006]
- Science and Technology Commission of Shanghai Municipality [17JC1405000]
- NSF under the CCI Center for Selective C-H Functionalization [CHE-1205646]
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One formidable challenge in sp(2) C-H activation is how to achieve high para selectivity on electron-deficient arenes because such site selectivity is disfavored by the electronic bias induced by the electron-withdrawing groups. The first highly selective para-C-H acetoxylation of various benzoic acids using a nitrile-based template was realized. Removal of the template leads to para-hydroxylated benzoic acids, which are versatile intermediates for a wide range of synthetically useful transformations.
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