61971-91-3Relevant articles and documents
DABCO-promoted photocatalytic C-H functionalization of aldehydes
Cardozo, Thiago Messias,Da Silva Santos, Bruno Maia,Finelli, Fernanda Gadini,de Souza, Cauê Paula,dos Santos Dupim, Mariana
supporting information, p. 2959 - 2967 (2022/01/12)
Herein we present a direct application of DABCO, an inexpensive and broadly accessible organic base, as a hydrogen atom transfer (HAT) abstractor in a photocatalytic strategy for aldehyde C-H activation. The acyl radicals generated in this step were arylated with aryl bromides through a well stablished nickel cross-coupling methodology, leading to a variety of interesting aryl ketones in good yields. We also performed computational calculations to shine light in the HAT step energetics and determined an optimized geometry for the transition state, showing that the hydrogen atom transfer between aldehydes and DABCO is a mildly endergonic, yet sufficiently fast step. The same calculations were performed with quinuclidine, for comparison of both catalysts and the differences are discussed.
Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 7624 - 7629 (2019/10/02)
A highly reactive catalytic system for the carbonylative coupling of aryl iodides with alkenylaluminum reagents has been developed. Various β-substituted γ,δ-unsaturated ketones were produced under mild conditions in good to excellent yields even under ppm level of palladium catalyst. Notably, this also represents the first example on carbonylative transformation of alkenylaluminum compounds. Additionally, by the addition of zinc salt, the selectivity of the product can be modified.
Halogen-bonded iodonium ion catalysis: A route to α-hydroxy ketones: Via domino oxidations of secondary alcohols and aliphatic C-H bonds with high selectivity and control
Guha, Somraj,Kazi, Imran,Mukherjee, Pranamita,Sekar, Govindasamy
supporting information, p. 10942 - 10945 (2017/10/13)
A domino synthesis of α-hydroxy ketones has been developed from benzylic secondary alcohols employing catalytic iodonium ions stabilized by DMSO. The reaction proceeds through an unprecedented sequential oxidation of alcohols to ketone and its α-hydroxylation in a controlled manner. The spectroscopic evidence establishes the possibility of formation of a stable halogen-bonded adduct between DMSO and iodonium ions.