Direct Synthetic Route to Functionalized 1, 2‐Azaborinines1. Issue 13 (26th February 2014)

• Record Type: Journal Article
• Authors: Braunschweig, Holger; Geetharani, K.; Jimenez‐Halla, J. Oscar C.; Schäfer, Marius
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 13(2014)
• Page Start: 3500
• Page End: 3504
• Publication Date: 2014-02-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201309707
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new catalytic synthetic route to functionalized 1, 2‐azaborinines has been developed by the [2+2]/[2+4] cycloaddition reactions of di‐tert‐butyliminoboranes and alkynes in presence of a rhodium catalyst. The first examples of ferrocene‐functionalized azaborinines have been synthesized using this strategy. Moreover, the regioselectivity of this reaction can be controlled by the formation of an intermediate rhodium 1, 2‐azaborete complex, which results in the isolation of the first azaborinine boronic ester. The isolation of an NH‐containing BN isostere by elimination of isobutene from an N(<italic>t</italic>Bu) group under thermolytic conditions has also been achieved. Theoretical studies give further insight into the formation of 1, 2‐azaborinines and the elimination of isobutene from the N(<italic>t</italic>Bu) group.</p> </abstract>