1007561-82-1Relevant articles and documents
Metal-free borylative dearomatization of indoles: Exploring the divergent reactivity of aminoborane C-H borylation catalysts
Jayaraman, Arumugam,Misal Castro, Luis C.,Desrosiers, Vincent,Fontaine, Frédéric-Georges
, p. 5057 - 5063 (2018)
While the dearomatization of indoles by carbon-boron bond forming reactions is new and quite promising, they are so far mainly metal-catalyzed. Here, we establish the use of metal-free catalysts in promoting such reactions in an atom-efficient way. The in situ generated ambiphilic aminoborane catalyst (1-Pip-2-BH2-C6H4)2 (Pip = piperidyl) promotes borylative dearomatization of various 1-arylsulfonyl indoles with pinacolborane in a syn addition fashion, with H and Bpin groups added respectively to the 2 and 3 positions of indoles. Catalysis proceeds with good to excellent conversion and essentially with complete regio- and diastereoselectivity. From mechanistic insights and DFT computations, we realized and established that prototypical boranes can also catalyze this borylative dearomatization.
Heterocycles from ylides. Part X.Synthesis of 3-hydroxy-2,3-dihydroindoles by a domino reaction
Cremonesi, Giuseppe,Croce, Piero Dalla,Fontana, Francesco,La Rosa, Concetta
experimental part, p. 873 - 876 (2009/09/28)
A domino reaction between 2-N-phenylsulfonylaminobenzaldehyde (1) and sulfonium ylides (2) leads to 3-hydroxy-2,3-dihydroindoles (3) whose structure was confirmed on the basis of analytical and spectroscopic data.