Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds

Using the [Ru­(p-cymene)­Cl2]2 (1) complex, catalytic hydroboration of aldehydes and ketones with pinacolborane under neat and mild conditions is reported. At rt, chemoselective hydroboration of aldehydes over the ketones is also attained. Mechanistic studies confirmed the immediate formation of mon...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 17; no. 19; pp. 4790 - 4793
Main Authors Kaithal, Akash, Chatterjee, Basujit, Gunanathan, Chidambaram
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
ALKENES
CROSS-COUPLING REACTIONS
ASYMMETRIC REDUCTION
ENANTIOSELECTIVE REDUCTION
ZN(II) COMPLEX
CATECHOLBORANE
ALDEHYDES
HALO BORONIC ESTERS
BORYL COMPLEXES
Online AccessGet full text

Cover

More Information
Summary:Using the [Ru­(p-cymene)­Cl2]2 (1) complex, catalytic hydroboration of aldehydes and ketones with pinacolborane under neat and mild conditions is reported. At rt, chemoselective hydroboration of aldehydes over the ketones is also attained. Mechanistic studies confirmed the immediate formation of monohydride bridged dinuclear complex [{(η6-p-cymene)­RuCl}2­(μ-H-μ-Cl)] (1b) from the reaction of 1 with pinacolborane, which catalyzed the highly efficient hydroboration reactions. The catalytic cycle containing mononuclear Ru–H species and intramolecular 1,3-hydride transfer is postulated.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02352