Recent Advances in Catalytic Dearomative Hydroboration of N-Heteroarenes

Sehoon Park

doi:10.1002/cctc.201902303

Recent Advances in Catalytic Dearomative Hydroboration of N-Heteroarenes

Sehoon Park^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Review article › peer-review

28 Scopus citations

Abstract

Catalytic dearomative reduction of N-heteroarenes is of important transformations in organic synthesis as well as medicinal chemistry, since the reduced aza compounds such as dihydropyridines can be synthetic building blocks as well as structural motifs for bioactive natural products and pharmaceuticals. While hydrogenation and hydrosilylation are well-utilized methods for such dearomative reduction of N-heteroarenes, the dearomative hydroboration has recently emerged as a competent alternative with high selectivity and good functional group tolerance. This Minireview describes recent advances in the catalytic hydroboration of N-heteroarenes. A diverse range of new catalytic systems will be detailed with strong emphasis on their unique working modes, which are closely related to chemo-, regio- and stereooutcomes observed in the hydroboration of N-heteroarenes.

Original language	English
Pages (from-to)	3170-3185
Number of pages	16
Journal	ChemCatChem
Volume	12
Issue number	12
DOIs	https://doi.org/10.1002/cctc.201902303
State	Published - 18 Jun 2020

Keywords

N-heteroarenes
catalytic reduction
dearomatization
hydride transfer pathway
hydroboration

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10.1002/cctc.201902303

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abstract = "Catalytic dearomative reduction of N-heteroarenes is of important transformations in organic synthesis as well as medicinal chemistry, since the reduced aza compounds such as dihydropyridines can be synthetic building blocks as well as structural motifs for bioactive natural products and pharmaceuticals. While hydrogenation and hydrosilylation are well-utilized methods for such dearomative reduction of N-heteroarenes, the dearomative hydroboration has recently emerged as a competent alternative with high selectivity and good functional group tolerance. This Minireview describes recent advances in the catalytic hydroboration of N-heteroarenes. A diverse range of new catalytic systems will be detailed with strong emphasis on their unique working modes, which are closely related to chemo-, regio- and stereooutcomes observed in the hydroboration of N-heteroarenes.",

keywords = "N-heteroarenes, catalytic reduction, dearomatization, hydride transfer pathway, hydroboration",

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AB - Catalytic dearomative reduction of N-heteroarenes is of important transformations in organic synthesis as well as medicinal chemistry, since the reduced aza compounds such as dihydropyridines can be synthetic building blocks as well as structural motifs for bioactive natural products and pharmaceuticals. While hydrogenation and hydrosilylation are well-utilized methods for such dearomative reduction of N-heteroarenes, the dearomative hydroboration has recently emerged as a competent alternative with high selectivity and good functional group tolerance. This Minireview describes recent advances in the catalytic hydroboration of N-heteroarenes. A diverse range of new catalytic systems will be detailed with strong emphasis on their unique working modes, which are closely related to chemo-, regio- and stereooutcomes observed in the hydroboration of N-heteroarenes.

KW - N-heteroarenes

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Recent Advances in Catalytic Dearomative Hydroboration of N-Heteroarenes

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