189579-55-3Relevant articles and documents
Efficient Docking–Migration Strategy for Selective Radical Difluoromethylation of Alkenes
Yu, Jiajia,Wu, Zhen,Zhu, Chen
, p. 17156 - 17160 (2018)
Radical-mediated difunctionalization of alkenes is a powerful tactic for olefin utilization. However, the transformation of unactivated alkenes still remains a formidable challenge. Now a conceptually new docking–migration strategy is presented for the difunctionalization of alkenes with photoredox catalysis. Both activated and unactivated alkenes are suitable substrates. A vast array of functional groups are compatible with the mild reaction conditions. Heteroaryl and difluoromethyl are concomitantly incorporated into alkenes, leading to synthetically valuable products that are readily converted into a variety of fluorine-containing molecules. The protocol provides a kinetic control of stereoselectivity for cycloalkenes to generate the unusual cis-products, and offers an efficient approach for the late-stage functionalization of complex natural products and drug molecules. A portfolio of dual-function reagents are prepared for the elusive radical difunctionalization of alkenes.
(Fluoromethylsulfonyl)methylation of Quinoxalinones Using NaSO2CH2F for C-F Bond Cleavage
Dai, Peng,Li, Yufei,Chen, Yu,Jiao, Jian,Wang, Qingqing,Li, Chenxiao,Gu, Yucheng,Zhang, Yanbin,Xia, Qing,Zhang, Wei-Hua
supporting information, p. 1357 - 1361 (2022/02/14)
We developed a facile, efficient, and scalable route to achieve monofluoromethylsulfinyl alkylation of quinoxalinones. NaSO2CH2F served as the source of methylene to construct new C-C and C-S bonds via C-F bond cleavage. NaSO2CH2F was also the source of SO2CH2F. Density functional theory calculations confirmed the proposed mechanism, in which the SO2CH2F radical is immediately trapped. The reaction exhibited a high level of atom economy. Moreover, some representative products displayed excellent biological activity.
Direct and Chemoselective Electrophilic Monofluoromethylation of Heteroatoms (O-, S-, N-, P-, Se-) with Fluoroiodomethane
Senatore, Raffaele,Malik, Monika,Spreitzer, Markus,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 1345 - 1349 (2020/02/13)
The commercially available fluoroiodomethane represents a valuable and effective electrophilic source for transferring the CH2F unit to a series of heteroatom-centered nucleophiles under mild basic conditions. The excellent manipulability offered by its liquid physical state (bp 53.4 °C) enables practical and straightforward one-step nucleophilic substitutions to retain the chiral information embodied, thus allowing it to overcome de facto the requirement for fluoromethylating agents with no immediate access. The high-yielding methodology was successfully applied to a variety of nucleophiles including a series of drugs currently in the market.
