Issue 62, 2020
From the journal:

Chemical Communications

Multicomponent benzannulation of allylic P-ylides with isocyanates or aldehydes for construction of anilines and biaryls†

Kaki Raveendra Babu,a   Yang Li,a   Wenbo Xu,*b   Yuhai Tang,a   Wenquan Zhang ORCID logo *c  and  Silong Xu ORCID logo *a  

* Corresponding authors

a School of Chemistry, Xi’an Key Laboratory of Sustainable Energy Materials Chemistry, and Shaanxi Quantong Joint Research Institute of New Energy Vehicles Power, Xi’an Jiaotong University, Xi’an 710049, P. R. China
E-mail: longxu@mail.xjtu.edu.cn

b College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China
E-mail: xuwenbo@sdnu.edu.cn

c Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), Mianyang 621900, P. R. China
E-mail: zhangwq-cn@caep.cn

Abstract

The reactivity of allylic phosphorus ylides generated in situ from alkoxycarbonylmethylenephosphoranes and propiolates is investigated toward isocyanates and aromatic aldehydes, which leads to one-pot multicomponent benzannulations for efficient synthesis of polysubstituted anilines and biaryls, respectively. The mechanism may involve a tandem [2+2] cycloaddition/fragmentation/Wittig/cyclization/elimination/aromatization sequence.

Graphical abstract: Multicomponent benzannulation of allylic P-ylides with isocyanates or aldehydes for construction of anilines and biaryls

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Article information

DOI
https://doi.org/10.1039/D0CC03461D
Article type
Communication
Submitted
15 May 2020
Accepted
28 Jun 2020
First published
29 Jun 2020

Chem. Commun., 2020,56, 8865-8868

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Multicomponent benzannulation of allylic P-ylides with isocyanates or aldehydes for construction of anilines and biaryls

K. R. Babu, Y. Li, W. Xu, Y. Tang, W. Zhang and S. Xu, Chem. Commun., 2020, 56, 8865 DOI: 10.1039/D0CC03461D

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