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Efficient Co-catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines.

07:00 EST 13th February 2020 | BioPortfolio

Summary of "Efficient Co-catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines."

The commercially available and bench-stable Co(acac)2/dpephos system is employed as a pre-catalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines (RN(BPin)2), which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.

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This article was published in the following journal.

Name: Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
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Organic compounds containing the -CN radical. The concept is distinguished from CYANIDES, which denotes inorganic salts of HYDROGEN CYANIDE.

Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.

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