Journal
ORGANIC LETTERS
Volume 20, Issue 17, Pages 5233-5237Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02184
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Funding
- Boston College
- ACS Green Chemistry Institute Pharmaceutical Roundtable [2016]
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An iron-catalyzed cross-coupling reaction between alkyl halides and arylboronic esters was developed that does not involve activation of the boronic ester with alkyllithium reagents nor requires magnesium additives. A combination of experimental and theoretical investigations revealed that lithium amide bases coupled with iron complexes containing deprotonated cyanobis(oxazoline) ligands were best to obtain high yields (up to 89%) in catalytic cross-coupling reactions. Mechanistic investigations implicate carbon-centered radical intermediates and highlight the critical importance of avoiding conditions that lead to iron aggregates. The new iron-catalyzed Suzuki-Miyaura reaction was applied toward the shortest reported synthesis of the pharmaceutical Cinacalcet.
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