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

Mandal, Dipendu; Hussain, Zahid; Luo, Yong-An; Wu, Yile; Stephan, Douglas W

Mandal, Dipendu; Hussain, Zahid; Luo, Yong-An; Wu, Yile; Stephan, Douglas W.

Afiliación

Mandal D; Institute of Drug Discovery Technology, Ningbo University, Zhejiang, 315211, China. wuyile@nbu.edu.cn.
Hussain Z; Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.
Luo YA; Institute of Drug Discovery Technology, Ningbo University, Zhejiang, 315211, China. wuyile@nbu.edu.cn.
Wu Y; Institute of Drug Discovery Technology, Ningbo University, Zhejiang, 315211, China. wuyile@nbu.edu.cn.
Stephan DW; Institute of Drug Discovery Technology, Ningbo University, Zhejiang, 315211, China. wuyile@nbu.edu.cn.

Chem Commun (Camb) ; 59(6): 780-783, 2023 Jan 17.

Article en En | MEDLINE | ID: mdl-36562320

RESUMEN

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 NîN double bond.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: China

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