1279722-88-1Relevant articles and documents
A traceless directing group for C - H borylation
Preshlock, Sean M.,Plattner, Donald L.,Maligres, Peter E.,Krska, Shane W.,Maleczka Jr., Robert E.,Smith III, Milton R.
, p. 12915 - 12919 (2013)
Not a trace: Borylation of the nitrogen in nitrogen heterocycles or anilines provides a traceless directing group for subsequent catalytic C - H borylation. Selectivities that previously required Boc protection can be achieved; furthermore, the NBpin directing group can be installed and removed in situ, and product yields are substantially higher. Boc=tert-butoxycarbonyl, pin=pinacolato. Copyright
I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines
Deng, Tianning,Shi, Emily,Thomas, Elana,Driver, Tom G.
supporting information, p. 9102 - 9106 (2020/11/13)
An I(III)-catalyzed oxidative cyclization-migration tandem reaction using Selectfluor as the oxidant was developed that converts unactivated anilines into 3H-indoles is reported herein. The reaction requires as little as 1 mol % of the iodocatalyst and is mild, tolerating pyridine and thiophene functional groups, and the dependence of the diastereoselectivity of the process on the identity of the iodoarene or iodoalkane precatalyst suggests that the catalyst is present for the stereochemical determining C-N bond forming step.
Control of the Chemoselectivity of Metal N-Aryl Nitrene Reactivity: C-H Bond Amination versus Electrocyclization
Kong, Chen,Jana, Navendu,Jones, Crystalann,Driver, Tom G.
supporting information, p. 13271 - 13280 (2016/10/22)
A mechanism study to identify the elements that control the chemoselectivity of metal-catalyzed N-atom transfer reactions of styryl azides is presented. Our studies show that the proclivity of the metal N-aryl nitrene to participate in sp3-C-H bond amination or electrocyclization reactions can be controlled by either the substrate or the catalyst. Electrocyclization is favored for mono-β-substituted and sterically noncongested styryl azides, whereas sp3-C-H bond amination through an H-atom abstraction-radical recombination mechanism is preferred when a tertiary allylic reaction center is present. Even when a weakened allylic C-H bond is present, our data suggest that the indole is still formed through an electrocyclization instead of a common allyl radical intermediate. The site selectivity of metal N-aryl nitrenes was found to be controlled by the choice of catalyst: Ir(I)-alkene complexes trigger electrocyclization processes while Fe(III) porphyrin complexes catalyze sp3-C-H bond amination in substrates where Rh2(II) carboxylate catalysts provide both products.
