Single and double activation of acetone by isolobal B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds

Chemical Science
Julian BöhnkeHolger Braunschweig

Abstract

B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds induce C-H activation of acetone to yield a (2-propenyloxy)aminoborane and an unsymmetrical 1-(2-propenyloxy)-2-hydrodiborene, respectively. DFT calculations showed that, despite their stark electronic differences, both the B[triple bond, length as m-dash]N and B[triple bond, length as m-dash]B triple bonds activate acetone via a similar coordination-deprotonation mechanism. In contrast, the reaction of acetone with a cAAC-supported diboracumulene yielded a unique 1,2,3-oxadiborole, which according to DFT calculations also proceeds via an unsymmetrical diborene, followed by intramolecular hydride migration and a second C-H activation of the enolate ligand.

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Citations

Mar 29, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Atsumi YagiMakoto Yamashita
Jul 3, 2019·Angewandte Chemie·Seiji AkiyamaMakoto Yamashita
Oct 24, 2019·Angewandte Chemie·Aishabibi KassymbekGeorgii I Nikonov
Oct 19, 2019·Angewandte Chemie·Zhenguo HuangHolger Braunschweig
Jul 7, 2018·Chemical Communications : Chem Comm·Lena WinnerHolger Braunschweig
Aug 27, 2021·Journal of the American Chemical Society·Andryj M BorysMichael J Cowley
Jan 15, 2019·Chemical Reviews·Marc-André LégaréHolger Braunschweig
Dec 11, 2021·Physical Chemistry Chemical Physics : PCCP·Domenik SchleierIngo Fischer
Jan 19, 2022·Dalton Transactions : an International Journal of Inorganic Chemistry·Ravi YadavSubrata Kundu

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Methods Mentioned

BETA
NMR
X-ray

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