20368-13-2Relevant articles and documents
Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes
Bai, Songlin,Gao, Yadong,Jiang, Chao,Liu, Xiaolei,Qi, Xiangbing,Wang, Jing,Wu, Qingcui,Yang, Chao
, p. 675 - 688 (2020/03/11)
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Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
Kaiser, Daniel,Teskey, Christopher J.,Adler, Pauline,Maulide, Nuno
supporting information, p. 16040 - 16043 (2017/11/22)
A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung via N-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolates. The method conveys broad functional group tolerance on both components, does not suffer from formation of homocoupling byproducts and avoids the use of transition metal catalysts.
Rh(I)-Catalyzed Hydroamidation of Olefins via Selective Activation of N-H Bonds in Aliphatic Amines
Dong, Kaiwu,Fang, Xianjie,Jackstell, Ralf,Laurenczy, Gabor,Li, Yuehui,Beller, Matthias
supporting information, p. 6053 - 6058 (2015/05/27)
Hydroamidation of olefins constitutes an ideal, atom-efficient method to prepare carboxylic amides from easily available olefins, CO, and amines. So far, aliphatic amines are not suitable for these transformations. Here, we present a ligand- and additive-free Rh(I) catalyst as solution to this problem. Various amides are obtained in good yields and excellent regioselectivities. Notably, chemoselective amidation of aliphatic amines takes place in the presence of aromatic amines and alcohols. Mechanistic studies reveal the presence of Rh-acyl species as crucial intermediates for the selectivity and rate-limiting step in the proposed Rh(I)-catalytic cycle. (Chemical Formula Presented).