67752-32-3Relevant academic research and scientific papers
Synthesis of [5,6]-Bicyclic Heterocycles with a Ring-Junction Nitrogen Atom: Rhodium(III)-Catalyzed C?H Functionalization of Alkenyl Azoles
Halskov, Kim S?holm,Roth, Howard S.,Ellman, Jonathan A.
, p. 9183 - 9187 (2017)
The first syntheses of privileged [5,6]-bicyclic heterocycles, with ring-junction nitrogen atoms, by transition metal catalyzed C?H functionalization of C-alkenyl azoles is disclosed. Several reactions are applied to alkenyl imidazoles, pyrazoles, and triazoles to provide products with nitrogen incorporated at different sites. Alkyne and diazoketone coupling partners give azolopyridines with various substitution patterns. In addition, 1,4,2-dioxazolone coupling partners yield azolopyrimidines. Furthermore, the mechanisms for the reactions are discussed and the utility of the developed approach is demonstrated by iterative application of C?H functionalization for the rapid synthesis of a patented drug candidate.
Electrochemical Hydrogenation with Gaseous Ammonia
Li, Jin,He, Lingfeng,Liu, Xu,Cheng, Xu,Li, Guigen
supporting information, p. 1759 - 1763 (2019/01/16)
As a carbon-free and sustainable fuel, ammonia serves as high-energy-density hydrogen-storage material. It is important to develop new reactions able to utilize ammonia as a hydrogen source directly. Herein, we report an electrochemical hydrogenation of alkenes, alkynes, and ketones using ammonia as the hydrogen source and carbon electrodes. A variety of heterocycles and functional groups, including for example sulfide, benzyl, benzyl carbamate, and allyl carbamate were well tolerated. Fast stepwise electron transfer and proton transfer processes were proposed to account for the transformation.
Base-Controlled Completely Selective Linear or Branched Rhodium(I)-Catalyzed C?H ortho-Alkylation of Azines without Preactivation
Tran, Ga?l,Hesp, Kevin D.,Mascitti, Vincent,Ellman, Jonathan A.
supporting information, p. 5899 - 5903 (2017/05/12)
A [RhI]/bisphosphine/base catalytic system for the ortho-selective C?H alkylation of azines by acrylates and acrylamides is reported. This catalytic system features an unprecedented complete linear or branched selectivity that is solely dependent on the catalytic base that is used. Complete branched selectivity is even achieved for ethyl methacrylate, which enables the introduction of a quaternary carbon center. Excellent functional group compatibility is demonstrated for both linear and branched alkylations. The operational simplicity and broad scope of this transformation allow for rapid access to functionalized azines of direct pharmaceutical and agrochemical relevance.
