1607016-07-8Relevant academic research and scientific papers
Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines
Gil-Negrete, José M.,Pérez Sestelo, José,Sarandeses, Luis A.
, p. 9778 - 9785 (2019/08/28)
Triorganoindium reagents (R3In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph3CBF4 as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.
Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates
Xie, Zhiyu,Liu, Lei,Chen, Wenfang,Zheng, Hongbo,Xu, Qingqing,Yuan, Huiqing,Lou, Hongxiang
supporting information, p. 3904 - 3908 (2014/05/06)
Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.
A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate
Chen, Wenfang,Zheng, Hongbo,Pan, Xinhui,Xie, Zhiyu,Zan, Xin,Sun, Bin,Liu, Lei,Lou, Hongxiang
supporting information, p. 2879 - 2882 (2014/05/06)
A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline with a variety of CH nucleophiles mediated by Na 2S2O8 is developed. The reaction proceeds smoothly to give the coupled product in up to 83%
