28143-79-5Relevant articles and documents
A base-controlled switch of SO2 reincorporation in photocatalyzed radical difunctionalization of alkenes
Bellotti, Peter,Glorius, Frank,Paulisch, Tiffany O.,Wang, Huamin,Zhang, Xiaolong
supporting information, p. 3412 - 3424 (2021/12/14)
Control of selectivity is a pivotal challenge in radical chemistry owing to the high reactivity and instability of radical species. Herein, a switchable, base-controlled strategy toward the reincorporation/release of SO2 in photocatalyzed radical difunctionalization of alkenes has been described. By this chemodivergent strategy, a variety of valuable, otherwise difficult-to-access γ-trifluoromethylated ketones and trifluoromethylated sulfonyl ketones can be selectively furnished from the same starting materials. This method features high chemoselectivity, a broad substrate scope, excellent functional group tolerance, and facile scale-up and was applied in a one-pot synthetic procedure. Evaluation of the reaction conditions and mechanistic studies indicate that the choice of base can invert the chemoselectivity of the reaction, demonstrating control over a challenging radical selectivity pattern.
α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation
González, Leticia,Maryasin, Boris,Maulide, Nuno,Mishevska, Magdalena,Teskey, Christopher J.,V?lkl, Martin,Zawodny, Wojciech
supporting information, p. 20935 - 20939 (2020/10/02)
Triflic anhydride mediated activation of acetophenones leads to highly electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α-arylated and α-oxyamina
Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3
Tummatorn, Jumreang,Punjajom, Kunlayanee,Rodphon, Warabhorn,Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Lumyong, Kanyapat,Thongsornkleeb, Charnsak,Nimnual, Phongprapan,Ruchirawat, Somsak
supporting information, p. 4694 - 4697 (2019/06/27)
1,1-Disubstituted vinyl triflates are synthesized by direct hydrotriflation of terminal alkynes employing a combination of TfOH and TMSN3 in DCM at room temperature. Interestingly, under these conditions, only terminal alkynes were selectively