573-46-6Relevant articles and documents
Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations
Yoon, Wan Seok,Han, Jung Tae,Yun, Jaesook
, p. 4953 - 4959 (2021/09/14)
A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).
Chiral electron-rich PNP ligand with a phospholane motif: Structural features and application in asymmetric hydrogenation
Wang, Heng,Zhang, Yao,Yang, Tilong,Guo, Xiaochong,Gong, Quan,Wen, Jialin,Zhang, Xumu
, p. 8796 - 8801 (2020/11/13)
Despite the remarkable reactivity that was achieved by a series of transition-metal catalysts with a PNP type ligand, the electron-rich chiral PNP ligands have still been rarely reported because of the difficulties in synthesis and the nature of air-sensitivity. Herein, we report a novel chiral PNP ligand (Heng-PNP) with both a rigid backbone and a bulky tert-butyl group on the phospholane motif. We successfully obtained its divalent iron complex. The chiral environment of its Ir(III) complex was also discussed with quadrant analysis. This tridentate ligand was applied in iridium-catalyzed asymmetric hydrogenation of challenging diaryl ketones: up to 98% ee and 500 TON are achieved. Computational study showed that the twist of conjugate aryl group in the substrate (induced by the special chiral pocket of Ir/Heng-PNP complex) leads to the energy difference in the enantiodetermining step.
Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes
Wei, Dong,Hu, Tian-Jiao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 743 - 748 (2018/07/25)
The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migration process is the key for success.