CuI Catalyzed Regio‐ and Stereo‐selective Hydroboration of Ynamides: α‐ and β‐Borylation via Hydro‐Cupration and Borylation

A CuI‐catalyzed hydrocupration and borylation protocol for the regio‐ and stereoselective borylation of ynamides utilizing pinacolatoborane (HBpin) as the borylating agent has been developed. The reaction features mild conditions, good substrate scope and functional group tolerance‐representing a hi...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2023-01, Vol.12 (1), p.n/a
Main Authors: Roy, Subhra, Mishra, Archana, Sekhar Pati, Subhransu, Behera, Minati, Prakash Das, Jaya
Format: Article
Language:English
Subjects:
Borylation
Functional groups
Hydroboration
Hydrocupration
Organic chemistry
Regioselectivity
Stereoselectivity
Substrates
vinylboronates
ynamides
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Summary:A CuI‐catalyzed hydrocupration and borylation protocol for the regio‐ and stereoselective borylation of ynamides utilizing pinacolatoborane (HBpin) as the borylating agent has been developed. The reaction features mild conditions, good substrate scope and functional group tolerance‐representing a highly efficient and practical method for the synthesis of regio‐ and stereoselective tri‐substituted alkenylboronates from readily available ynamides. The regioselectivity is controlled by altering substituents on the ynamides (alkyl vs aryl) and utilizing a catalytic species [LCuH] generated in situ from HBpin and [LCuX]. Suzuki coupling and other transformations highlight the synthetic utility of the method. A CuI catalyzed regio‐ and stereoselective hydroboration reaction of ynamides have been developed where the selectivity between α‐ and β‐Borylation is tuned by altering substituent on the ynamides.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200505