Journal
SCIENCE
Volume 343, Issue 6176, Pages 1216-1220Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1249198
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Funding
- Scripps Research Institute
- NIH (National Institute of General Medical Sciences) [2R01GM084019]
- Bristol-Myers Squibb
- Sichuan University
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The use of ligands to tune the reactivity and selectivity of transition metal catalysts for C(sp(3))-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp(3))-H arylation using pyridine and quinoline derivatives: The former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of beta-Ar-beta-Ar'-alpha-amino acids with excellent levels of diastereoselectivity (diastereomeric ratio > 20:1). Both configurations of the beta-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp(3))-H olefination of a protected alanine.
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