- Iron-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Unactivated Arylboronic Esters
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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.
- Crockett, Michael P.,Tyrol, Chet C.,Wong, Alexander S.,Li, Bo,Byers, Jeffery A.
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supporting information
p. 5233 - 5237
(2018/09/12)
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- PROCESS FOR PREPARING CINACALCET HYDROCHLORIDE
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Processes for preparing cinacalcet are provided.
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Page/Page column 28
(2008/06/13)
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- Phenalkoxyalkyl- and phenoxyalkyl-substituted oxiranecarboxylic acids, their use and medicaments containing them
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Phenalkoxyalky- and phenoxyalkyl-substituted oxiranecarboxylic acids of the formula STR1 wherein R1 denotes a hydrogen atom (--H), a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group or a trifluoromethyl group, R2 has one of the meanings of R1, R3 denotes a hydrogen atom (--H) or a lower alkyl group, Y denotes --O--(CH2)m --, m denotes O or an integer from 1 to 4, and n denotes an integer from 2 to 8, with the proviso that the sum of m and n is an integer from 2 to 8, and the salts of the acids are new compounds. They display a hypoglycaemic action in warm-blooded animals. Processes for the preparation of the new compounds and of the intermediate products required for their preparation are described.
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