Journal
SCIENCE
Volume 351, Issue 6270, Pages 252-256Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aad7893
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Funding
- Scripps Research Institute
- NIH (National Institute of General Medical Sciences) [2R01GM084019]
- Wuhan University of Technology
- Jiangsu Normal University
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Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the beta or gamma positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.
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