725213-45-6Relevant articles and documents
LiHMDS-Promoted Palladium-Catalyzed Sonogashira Cross-Coupling of Aryl Fluorides with Terminal Alkynes
He, Jingjing,Yang, Kang,Zhao, Jianhong,Cao, Song
supporting information, p. 9714 - 9718 (2019/11/28)
A highly efficient Pd-catalyzed Sonogashira coupling of various aryl fluorides with terminal alkynes in the presence of LiHMDS was developed. Both unreactive electron-rich fluoroarenes and electron-poor fluoroarenes proceeded smoothly and afforded the cor
Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization
Pati, Kamalkishore,Michas, Christopher,Allenger, David,Piskun, Ilya,Coutros, Peter S.,Dos Passos Gomes, Gabriel,Alabugin, Igor V.
, p. 11706 - 11717 (2015/12/11)
The majority of Sn-mediated cyclizations are reductive and, thus, cannot give a fully conjugated product. This is a limitation in the application of Sn-mediated radical cascades for the preparation of fully conjugated molecules. In this work, we report an oxidatively terminated Bu3Sn-mediated cyclization of an alkyne where AIBN, the commonly used initiator, takes on a new function as an oxidative agent. Sn-mediated radical transformation of biphenyl aryl acetylenes into functionalized phenanthrenyl stannanes can be initiated via two potentially equilibrating vinyl radicals, one of which can be trapped by the fast 6-endoclosure at the biphenyl moiety in good to excellent yields. The efficient preparation of Sn-substituted phenanthrenes opens access to convenient building blocks for the construction of larger polyaromatics.
