857809-85-9Relevant articles and documents
Formal Lossen Rearrangement/[3+2] Annulation Cascade Catalyzed by a Modified Cyclopentadienyl RhIII Complex
Yamada, Takayuki,Shibata, Yu,Kawauchi, Susumu,Yoshizaki, Soichi,Tanaka, Ken
, p. 5723 - 5727 (2018)
It has been established that a cyclopentadienyl RhIII complex with two phenyl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/[3+2] annulation cascade of N-pivaloyl benzamides and acrylamides with alkynes leading to substituted indoles and pyrroles. Mechanistic studies revealed that this cascade reaction proceeds via not the Lossen rearrangement to form anilides or enamides but C?H bond cleavage, alkyne insertion, and the formal Lossen rearrangement.
Synthesis of indoles from aroyloxycarbamates with alkynes: Via decarboxylation/cyclization
Ma, Nuannuan,Li, Peihe,Wang, Zheng,Dai, Qipu,Hu, Changwen
supporting information, p. 2421 - 2426 (2018/04/12)
An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed to 2,3-disubstituted indoles directly. This protocol is further demonstrated by the efficient synthesis of indoles as well as the success of employing inexpensive aryl acids as starting materials to construct C-N bonds by releasing CO2.
