138352-27-9Relevant academic research and scientific papers
Addition/ring-opening reaction of organoboronic acids to cyclobutanones catalyzed by rhodium(I)/P(t-Bu)3 complex
Matsuda, Takanori,Makino, Masaomi,Murakami, Masahiro
, p. 1528 - 1533 (2005)
An addition/ring-opening reaction of aryl- and alkenylboronic acids to cyclobutanones took place in 1,4-dioxane at 100 °C in the presence of a rhodium(I) catalyst bearing tri-t-butylphosphine, affording ring-opened ketones. Mechanistically, the reaction proceeded through the addition of an organorhodium species to the carbonyl group of a cyclobutanone and a subsequent ring-opening of the resulting rhodium cyclobutanolate through β-carbon elimination. A deuterium-labeling experiment revealed that an alkylrhodium species generated by the β-carbon elimination underwent successive β-hydride elimination/re-addition processes to form the η3-oxaallylrhodium intermediate, which was readily protonated to afford the product.
