3070-40-4Relevant articles and documents
Development of BODIPY dyes with versatile functional groups at 3,5-positions from diacyl peroxides via Cu(ii)-catalyzed radical alkylation
Tang, Bing,Lv, Fan,Chen, Kangkang,Jiao, Lijuan,Liu, Qingyun,Wang, Hua,Hao, Erhong
, p. 4691 - 4694 (2019)
An efficient Cu(ii)-catalyzed, C-H alkylation of BODIPY with a variety of alkyl diacyl peroxides has been developed for the first time, providing a late-stage and straightforward method for controllable synthesis of monoalkylated and dialkylated BODIPYs via a radical process that otherwise is difficult to obtain by literature methods. This chemo- and site-selective transformation will allow for the introduction of a variety of functionalities on the BODIPY core for highly versatile tethering to receptors and to other molecules of interest.
Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds
Dong, Shunxi,Feng, Xiaoming,He, Jun,Liu, Wen,Liu, Xiaohua,Pu, Maoping,Wu, Yun-Dong,Zhang, Tinghui
supporting information, p. 11856 - 11863 (2021/08/16)
Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.
Radical alkylation of C(sp3)-H bonds with diacyl peroxides under catalyst-free conditions
Tian, Hao,Xu, Wentao,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 14813 - 14816 (2019/12/24)
Herein, we describe a protocol for alkylation reactions of C(sp3)-H bonds with diacyl peroxides by means of a process involving cross-coupling between an alkyl radical and an α-Aminoalkyl radical. The mild, catalyst-And additive-free conditions make this protocol superior to previously reported C(sp3)-H alkylation strategies. The protocol was applied to 1,2,3,4-Tetrahydroisoquinolines and a tetrahydro-β-carboline derivative and could be carried out on a gram scale, indicating its utility for the alkylation of late-stage synthetic intermediates.