28276-91-7Relevant articles and documents
Catalyst-free photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines
Duan, Wentao,Lian, Qi,Wang, Songping,Wei, Wentao,Zhou, Jingwei
supporting information, p. 3261 - 3267 (2021/05/21)
Due to the directional nature of sp3-hybridized orbitals and the absence of π-orbitals, the oxidative cleavage of the kinetically and thermodynamically stable C(sp3)-C(sp3) bond is extremely difficult and remains scarcely explored. In this work, under the double argument of quantum mechanics (QM) computations and meticulous experiments on our well-designed C-C single bond cleavage mechanism, we discovered a means of photoinduced selective oxidative C(sp3)-C(sp3) bond cleavage in arylamines, easily achieved by simple visible light irradiation using O2as a benign oxidant under very mild conditions. The utility of our methodology was demonstrated by the C(sp3)-C(sp3) bond cleavage in morpholine/piperazine arylamines with excellent functional group tolerance. Importantly, our methodology is noteworthy, not only in that it does not require any catalysts, but also in that it provides valuable possibilities for the scalable functionalization of clinical drugs and natural products.
Visible-Light-Mediated Aerobic Oxidative C(sp3)?C(sp3) Bond Cleavage of Morpholine Derivatives Using 4CzIPN as a Photocatalyst
Dong, Chun-Lin,Huang, Lan-Qian,Guan, Zhi,Huang, Chu-Sheng,He, Yan-Hong
supporting information, p. 3803 - 3811 (2021/06/28)
Herein, a metal-free strategy for the aerobic oxidative cleavage of the inert C(sp3)?C(sp3) bond was developed. Deconstruction of morpholine derivatives was conducted using visible light as an energy source and O2 as an oxidant under mild conditions. This procedure demonstrated suitable selectivity and functional group tolerance. Moreover, a possible mechanism involving a radical process was proposed based on a series of mechanism exploration and control experiments. (Figure presented.).
Practical Catalytic Cleavage of C(sp3)?C(sp3) Bonds in Amines
Li, Wu,Liu, Weiping,Leonard, David K.,Rabeah, Jabor,Junge, Kathrin,Brückner, Angelika,Beller, Matthias
supporting information, p. 10693 - 10697 (2019/07/09)
The selective cleavage of thermodynamically stable C(sp3)?C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper-based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα?Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.
