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Solvent-promoted catalyst-free regioselective N-incorporation multicomponent domino reaction: rapid assembly of π-functionalized [60]fullerene-fused dihydrocarbolines

Author:
Liu, Tong-Xin, Yue, Shuaishuai, Wei, Changgeng, Ma, Nana, Zhang, Pengling, Liu, Qingfeng, Zhang, Guisheng
Source:
Chemical communications 2018 v.54 no.95 pp. 13331-13334
ISSN:
1364-548X
Subject:
cleavage (chemistry), cycloaddition reactions, deprotonation, hydrocarbons, regioselectivity, solvents
Abstract:
Described here is the first example of solvent-promoted catalyst-free N-incorporation multicomponent domino reaction for the direct construction of novel π-extension [60]fullerene-fused dihydrocarbolines from simple hydrocarbons. This unprecedented transformation is proposed to proceed by a sequential N-incorporation/[4+2] cycloaddition/elimination process, involving multiple types of bond cleavage and formation in a single chemical operation. Mechanistic studies uncover that solvent is crucial for the success of the transformation, and multiple solvent-aided deprotonation and proton transfer are involved as key steps.
Agid:
6237924