Selective Ketone Formations via Cobalt-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols

Alcohols
Alcohols are organic compounds that are amongst the most recognizable and familiar, as they have wide-ranging applications and uses in everyday life. Alcohols are organic molecules containing a hydroxyl functional group connected to an alkyl or aryl group (ROH). If the hydroxyl carbon only has a single R group, it is known as primary alcohol. If it has two R groups, it is a secondary alcohol, and if it has three R groups, it is a tertiary alcohol. Like many other organic compounds,...

Source: Lara Al Hariri and Ahmed Basabrain at the University of Massachusetts Amherst, MA, USA

Source: Lara Al Hariri at the University of Massachusetts Amherst, MA, USA

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...

The preparation of SNS pincer cobalt(II) model complexes of liver alcohol dehydrogenase is presented here. The complexes can be prepared by reacting the ligand precursor with CoCl2·6H2O and can then be recrystallized by allowing diethyl ether to slowly diffuse into an acetonitrile solution that contains the cobalt...