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Preparation of Alcohols via Addition Reactions

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The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Published on: November 9, 2019

Alcohol Synthesis by Cobalt-Catalyzed Visible-Light-Driven Reductive Hydroformylation.

Connor S MacNeil¹, Lauren N Mendelsohn¹, Tyler P Pabst¹

¹Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|October 14, 2022

Summary

Cobalt catalysts enable reductive hydroformylation of alkenes using carbon monoxide and hydrogen. This process yields anti-Markovnikov alcohols with high regioselectivity, offering a new synthetic route.

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Area of Science:

Organometallic Chemistry
Catalysis
Organic Synthesis

Background:

Hydroformylation is a key industrial process for converting alkenes to aldehydes.
Developing selective and efficient catalytic systems remains an active area of research.
Reductive hydroformylation offers a direct route to alcohols, bypassing aldehyde isolation.

Purpose of the Study:

To describe a novel cobalt-catalyzed reductive hydroformylation of alkenes.
To achieve high yields and exclusive regiocontrol in the synthesis of one-carbon homologated alcohols.
To investigate the catalytic mechanism and origins of regioselectivity.

Main Methods:

Utilizing a cobalt hydride complex, (dcype)Co(CO)2H, activated by blue light irradiation.
Employing syngas (CO and H2) as the source of carbon monoxide and hydrogen.
In situ multinuclear NMR spectroscopy for mechanistic investigations.

Main Results:

Successful synthesis of one-carbon homologated alcohols from terminal and 1,1-disubstituted alkenes.
Achieved anti-Markovnikov product formation with yields ranging from 34-87%.
Demonstrated exclusive regiocontrol (linear/branch >99:1) for minimally functionalized alkenes.

Conclusions:

The developed cobalt catalyst system provides an efficient method for reductive hydroformylation.
The study elucidates the mechanistic basis for the observed absolute regiocontrol.
This work presents a valuable new tool for synthesizing functionalized alcohols.