Diverse functionalization of strong alkyl C–H bonds by undirected borylation | Zendy

Raphael J. Oeschger | Zendy; Bo Su | Zendy; Isaac Furay Yu | Zendy; Christian Ehinger | Zendy; Erik A. Romero | Zendy; Sam He | Zendy; John F. Hartwig | Zendy

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Diverse functionalization of strong alkyl C–H bonds by undirected borylation

Author(s) -

Raphael J. Oeschger,

Bo Su,

Isaac Furay Yu,

Christian Ehinger,

Erik A. Romero,

Sam He,

John F. Hartwig

Publication year - 2020

Publication title -

science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 12.556

H-Index - 1186

eISSN - 1095-9203

pISSN - 0036-8075

DOI - 10.1126/science.aba6146

Subject(s) - borylation , chemistry , reagent , alkyl , catalysis , hydrocarbon , iridium , ligand (biochemistry) , hydrogen bond , medicinal chemistry , hydride , photochemistry , combinatorial chemistry , hydrogen , organic chemistry , molecule , aryl , biochemistry , receptor

Speeding up borylation Catalytic borylation is the rare reaction that can selectively target stronger over weaker saturated carbon–hydrogen (C–H) bonds. However, the trade-off has been that the reaction is slow and requires high excess of the hydrocarbon. Oeschgeret al. now report that the right ligand (2-methylphenanthroline) coordinated to iridium can accelerate the reaction by 50- to 80-fold. This rate enhancement enables selective borylation of primary C–H bonds with the hydrocarbon as limiting reagent. The reaction is also unusually selective for β-C–H bonds in saturated heterocycles.Science , this issue p.736

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