836-05-5Relevant academic research and scientific papers
Metallaphotoredox-Catalyzed Cross-Electrophile Csp3-Csp3 Coupling of Aliphatic Bromides
Smith, Russell T.,Zhang, Xiaheng,Rincón, Juan A.,Agejas, Javier,Mateos, Carlos,Barberis, Mario,García-Cerrada, Susana,De Frutos, Oscar,Macmillan, David W. C.
supporting information, p. 17433 - 17438 (2019/01/04)
A strategy for the installation of small alkyl fragments onto pharmaceutically relevant aliphatic structures has been established via metallaphotoredox catalysis. Herein, we report that tris(trimethylsilyl)silanol can be employed as an effective halogen abstraction reagent that, in combination with photoredox and nickel catalysis, allows a generic approach to Csp3-Csp3 cross-electrophile coupling. In this study, we demonstrate that a variety of aliphatic drug-like groups can be successfully coupled with a number of commercially available small alkyl electrophiles, including methyl tosylate and strained cyclic alkyl bromides. Moreover, the union of two secondary aliphatic carbon centers, a long-standing challenge for organic molecule construction, has been accomplished with a wide array of structural formats. Last, this technology can be selectively merged with Csp2-Csp3 aryl-alkyl couplings to build drug-like systems in a highly modular fashion.
Stereoretentive copper(II)-catalyzed ritter reactions of secondary cycloalkanols
Al-Huniti, Mohammed H.,Lepore, Salvatore D.
supporting information, p. 3071 - 3076 (2014/03/21)
A Ritter-like coupling reaction of cyclic alcohols and both aryl and alkyl nitriles to form amides catalyzed by copper(II) triflate is described. These reactions proceed in good yields under mild and often solvent-free conditions. With 2-and 3-substituted
A direct and stereoretentive synthesis of amides from cyclic alcohols
Mondal, Deboprosad,Bellucci, Luca,Lepore, Salvatore D.
, p. 7057 - 7061 (2012/01/03)
Chlorosulfites prepared in situ using thionyl chloride react with nitrile complexes of titanium(IV) fluoride to give a one-pot conversion of alcohols into amides. For the first time, amides are obtained from cyclic alcohols with stereoretention. Critical to the design of these new TiIV reactions has been the use of little-explored TiIV nitrile complexes that are thought to chelate chlorosulfites in the transition state tocreate a carbocation that is rapidly captured by the nitrile nucleophile through a front-side attack mechanism.
