Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine.

ABSTRACT: Facile reduction of aryl halides with a combination of 5% Pd/C, B₂(OH)₄, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B₂(OD)₄ was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed

SUBMITTER: Korvinson KA 

PROVIDER: S-EPMC7566957 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature