Issue 6, 2023
From the journal:

Chemical Communications

Transient hydroboration and hydroalumination of activated azo-species: avenues to NBO and NAlO-heterobicycles†

Dipendu Mandal, ORCID logo ‡ab   Zahid Hussain,‡a   Yong-an Luo,a   Yile Wu ORCID logo *a  and  Douglas W. Stephan ORCID logo *ab  

* Corresponding authors

a Institute of Drug Discovery Technology, Ningbo University, Zhejiang, China
E-mail: wuyile@nbu.edu.cn

b Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada
E-mail: dstephan@chem.utoronto.ca

Abstract

Reactions of the boranes, BH(C6F5)2 or 9-BBN, with azodicarboxylates or an azodicarbonylamide provide facile access to NBO heterocyclic compounds. The products [(C6F5)2BOC(X)N]2 X = OEt 1, OiPr 2, OCH2CCl33, OCH2Ph 4, NC5H105) and [(9-BBN)OC(X)N]2 (X = OEt 6, OiPr 7, NC5H108) and [Ph2B)OC(OtBu)N]29 were prepared. In another variation, (nacnac)AlH2 (nacnac = (C6H3iPr2NC(Me))2CH) afforded the Al-heterobicycle [(nacnac)Al(H)OC(OEt)N]210. The mechanism for the formation of these products is proposed to involve transient hydroboration or hydroalumination of the N[double bond, length as m-dash]N double bond.

Graphical abstract: Transient hydroboration and hydroalumination of activated azo-species: avenues to NBO and NAlO-heterobicycles

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Article information

DOI
https://doi.org/10.1039/D2CC06207K
Article type
Communication
Submitted
16 Nov 2022
Accepted
15 Dec 2022
First published
16 Dec 2022

Chem. Commun., 2023,59, 780-783

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Transient hydroboration and hydroalumination of activated azo-species: avenues to NBO and NAlO-heterobicycles

D. Mandal, Z. Hussain, Y. Luo, Y. Wu and D. W. Stephan, Chem. Commun., 2023, 59, 780 DOI: 10.1039/D2CC06207K

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