60770-67-4Relevant academic research and scientific papers
Metal-free transfer hydrochlorination of internal C-C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride
Oestreich, Martin,Weidkamp, Andreas J.
supporting information, p. 973 - 976 (2022/02/01)
The development and application of a transfer hydrochlorination reagent based on a trichlorinated bicyclo[3.1.0]hexane core that transfers two molecules of HCl per molecule of surrogate to a π-basic substrate under B(C6F5)3 catalysis is reported. Lewis acid-assisted chloride abstraction followed by thermal electrocyclic cyclopropyl-to-allyl cation ring opening releases ring strain as a previously unexploited driving force.
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information, p. 17211 - 17217 (2021/07/02)
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.
Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
supporting information, p. 11187 - 11190 (2019/09/30)
A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
