Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 7, Pages 2825-2832Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b13346
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- Graduate School at Princeton University
- Natural Sciences and Engineering Research Council of Canada
- NIH [R01 GM121441]
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Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp(2))-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-((PNP)-P-iPr)Co(H)(2)BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-((PNP)-P-iPr)Co((O2CBu)-Bu-t)(2) (2) compounds were effective and exhibited broad functional group tolerance across a wide range of fluoroarenes containing electronically diverse functional groups, regardless of the substitution pattern on the arene. The electronically enhanced ortho-to-fluorine selectivity observed with the cobalt catalysts was maintained in the presence of a benzylic dimethylamine and hydrosilanes, overriding the established directing-group effects observed with precious-metal catalysts. The synthetically useful selectivity observed with cobalt was applied to an efficient synthesis of the anti-inflammatory drug flurbiprofen.
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