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Catalytic Nitrile Hydroboration: A Route to N,N-Diborylamines and Uses Thereof.
Chem Asian J. 2020 Jul 06 [Online ahead of print]CA

Abstract

Catalytic reduction of nitriles is considered as an attractive and atom-economical route to a diversity of synthetically valuable primary amines. Compared to other methods, dihydroboration approach has been developed relatively recently but has already attracted the attention of many research groups due to reasonably mild reaction conditions, selectivity control and the access to N,N-diborylamines, which emerged as powerful reagents for C-N bond forming reactions. Early developments in catalytic dihydroboration of nitriles implied precious metal catalysts along with harsh conditions and prolonged reaction times, whereas recent advances mostly rely on base and main group metal catalytic systems with significantly improved profiles. This minireview aims to provide an overview of advances and challenges of dihydroboration of nitriles with d-, f- and main group metal catalysts. Mechanistic features of different catalytic systems, functional group tolerance and scope of the methods are also presented. The synthetic utility of N,N-diborylamies, beyond simple protodeborylation, is discussed in the aspect of N-arylation, imine and amide synthesis.

Authors+Show Affiliations

Department of Chemistry School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Avenue, Nur-Sultan, 010000, Kazakhstan.Department of Chemistry School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Avenue, Nur-Sultan, 010000, Kazakhstan. The Environment and Resource Efficiency Cluster (EREC), Nazarbayev University, 53 Kabanbay Batyr Avenue, Nur-Sultan, 010000, Kazakhstan.

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

32627941

Citation

Hayrapetyan, Davit, and Andrey Y. Khalimon. "Catalytic Nitrile Hydroboration: a Route to N,N-Diborylamines and Uses Thereof." Chemistry, an Asian Journal, 2020.
Hayrapetyan D, Khalimon AY. Catalytic Nitrile Hydroboration: A Route to N,N-Diborylamines and Uses Thereof. Chem Asian J. 2020.
Hayrapetyan, D., & Khalimon, A. Y. (2020). Catalytic Nitrile Hydroboration: A Route to N,N-Diborylamines and Uses Thereof. Chemistry, an Asian Journal. https://doi.org/10.1002/asia.202000672
Hayrapetyan D, Khalimon AY. Catalytic Nitrile Hydroboration: a Route to N,N-Diborylamines and Uses Thereof. Chem Asian J. 2020 Jul 6; PubMed PMID: 32627941.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic Nitrile Hydroboration: A Route to N,N-Diborylamines and Uses Thereof. AU - Hayrapetyan,Davit, AU - Khalimon,Andrey Y, Y1 - 2020/07/06/ PY - 2020/06/07/received PY - 2020/07/03/revised PY - 2020/7/7/pubmed PY - 2020/7/7/medline PY - 2020/7/7/entrez KW - borylamines KW - hydroboration KW - main group elements KW - nitriles KW - transition metals JF - Chemistry, an Asian journal JO - Chem Asian J N2 - Catalytic reduction of nitriles is considered as an attractive and atom-economical route to a diversity of synthetically valuable primary amines. Compared to other methods, dihydroboration approach has been developed relatively recently but has already attracted the attention of many research groups due to reasonably mild reaction conditions, selectivity control and the access to N,N-diborylamines, which emerged as powerful reagents for C-N bond forming reactions. Early developments in catalytic dihydroboration of nitriles implied precious metal catalysts along with harsh conditions and prolonged reaction times, whereas recent advances mostly rely on base and main group metal catalytic systems with significantly improved profiles. This minireview aims to provide an overview of advances and challenges of dihydroboration of nitriles with d-, f- and main group metal catalysts. Mechanistic features of different catalytic systems, functional group tolerance and scope of the methods are also presented. The synthetic utility of N,N-diborylamies, beyond simple protodeborylation, is discussed in the aspect of N-arylation, imine and amide synthesis. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/32627941/Catalytic_Nitrile_Hydroboration:_A_Route_to_N,N-Diborylamines_and_Uses_Thereof L2 - https://doi.org/10.1002/asia.202000672 DB - PRIME DP - Unbound Medicine ER -
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