Journal
SCIENCE
Volume 368, Issue 6492, Pages 736-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aba6146
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Funding
- National Institutes of Health (NIH) [R35GM130387]
- NIH [S10OD024998]
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The selective functionalization of strong, typically inert carbon-hydrogen (C-H) bonds in organic molecules is changing synthetic chemistry. However, the undirected functionalization of primary C-H bonds without competing functionalization of secondary C-H bonds is rare. The borylation of alkyl C-H bonds has occurred previously with this selectivity, but slow rates required the substrate to be the solvent or in large excess. We report an iridium catalyst ligated by 2-methylphenanthroline with activity that enables, with the substrate as limiting reagent, undirected borylation of primary C-H bonds and, when primary C-H bonds are absent or blocked, borylation of strong secondary C-H bonds. Reactions at the resulting carbon-boron bond show how these borylations can lead to the installation of a wide range of carboncarbon and carbon-heteroatom bonds at previously inaccessible positions of organic molecules.
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