1446319-69-2Relevant academic research and scientific papers
A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles
Zhou, Shuguang,Wang, Jinhu,Zhang, Feifei,Song, Chao,Zhu, Jin
supporting information, p. 2427 - 2430 (2016/06/09)
A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.
Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant
Zhou, Shuguang,Wang, Jinhu,Chen, Pei,Chen, Kehao,Zhu, Jin
supporting information, p. 14508 - 14512 (2016/10/03)
A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.
Rhodium(III)-catalyzed indole synthesis using N-N bond as an internal oxidant
Liu, Baoqing,Song, Chao,Sun, Chao,Zhou, Shuguang,Zhu, Jin
, p. 16625 - 16631 (2013/12/04)
We report herein a Rh(III)-catalyzed cyclization of N-nitrosoanilines with alkynes for streamlined synthesis of indoles. The synthetic protocol features a distinct internal oxidant, N-N bond, as a reactive handle for catalyst turnover, as well as a hitherto tantalizingly elusive intermolecular redox-neutral manifold, predicated upon C-H activation, for the formation of a five-membered azaheterocycle. The compatibility of seemingly dichotomous acidic and basic conditions ensures reaction versatility for multifarious synthetic contexts. The tolerance of an array of auxiliary functional groups potentially permits predefined, programmable substitution patterns to be incorporated into the indole scaffold. Comprehensive mechanistic studies, under acidic condition, support [RhCp*]2+ as generally the catalyst resting state (switchable to [RhCp*(OOCtBu)]+ under certain circumstance) and C-H activation as the turnover-limiting step. Given the variety of covalent linkages available for the nitroso group, this labile functionality is likely to be harnessed as a generic handle for strikingly diverse coupling reactions.
Reactivity of tetrahydrochromeno[2,3-b]indoles: Chromic indicators of cyanide
Douglas, Nicholas,Neef, Charles J.,Rogers, Robert A.,Stanley, Jake A.,Armitage, Jacob,Martin, Ben,Hudnall, Todd W.,Brittain, William J.
, p. 688 - 695 (2013/08/23)
The synthesis and reactivity of a tetrahydrochromeno[2,3-b]indoles are reported. Evidence for reversible ring-opening is based on H/D exchange and trapping experiments. These compounds readily undergo reaction with tetra-n-butylammonium cyanide. The cyanide reaction is 10-100× faster when the solution is irradiated with 350 nm light. Reaction with trimethylsilyl cyanide occurs only with UV irradiation demonstrating photoreactivity. The rate of tetrahydrochromeno[2,3-b]indole ring-opening is greater for (i) Me substitution at the hemiaminal carbon (compared to Ph), and (ii) substitution of fluorine at the 9-position of the indole. Under acidic conditions, the ring-opened indolium ion is observed. Copyright
