AI Article Synopsis
- Vinylidene rearrangement of alkynes is a powerful method for transforming alkynes, but the application of borylalkynes in this process has not been extensively studied.
- This research explores the rearrangement of internal borylalkynes using a cationic ruthenium complex, highlighting that the reaction is effective for both tri- and tetracoordinate boryl groups, with reaction rates significantly influenced by the Lewis acidity of the boryl group.
- The study found that the rearrangement involves 1,2-boryl migration and showed that tricoordinate boryl groups migrate via an electrophilic process, contrasting with previous methods involving vinylidene rearrangements of internal alkyn
Article Abstract
Vinylidene rearrangement of alkynes is a well-established and powerful method for alkyne transformations, while use of borylalkynes has remained largely unexplored. This paper describes vinylidene rearrangements of internal borylalkynes using a cationic ruthenium complex. This rearrangement is applicable to alkynes with both tri-(B(pin), B(dan)) and tetracoordinate (B(mida)) boryl groups, and the reaction rate is dramatically affected by the Lewis acidity of the boryl group. Mechanistic study revealed that the rearrangement proceeds 1,2-boryl migration regardless of the coordination number of the boron center. The migration mode was elucidated by theoretical calculations to indicate that the migration of the tricoordinate boryl groups is an electrophilic process in contrast to the previous vinylidene rearrangements of internal alkynes with two carbon substituents.
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| http://dx.doi.org/10.1039/d4dt01042f | DOI Listing |
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