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Issue 95, 2018
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Solvent-promoted catalyst-free regioselective N-incorporation multicomponent domino reaction: rapid assembly of π-functionalized [60]fullerene-fused dihydrocarbolines

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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.

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

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Article information


Submitted
19 Sep 2018
Accepted
15 Oct 2018
First published
15 Oct 2018

Chem. Commun., 2018,54, 13331-13334
Article type
Communication

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

T. Liu, S. Yue, C. Wei, N. Ma, P. Zhang, Q. Liu and G. Zhang, Chem. Commun., 2018, 54, 13331
DOI: 10.1039/C8CC07580H

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