Recent Advances in Catalytic Dearomative Hydroboration of N‐Heteroarenes. Issue 12 (30th March 2020)

• Record Type: Journal Article
• Authors: Park, Sehoon
• Is Part Of: ChemCatChem. Volume 12:Issue 12(2020)
• Page Start: 3170
• Page End: 3185
• Publication Date: 2020-03-30
• Subjects: catalytic reduction -- dearomatization -- hydroboration -- N-heteroarenes -- hydride transfer pathway; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201902303
• Languages: English
• ISSNs: 1867-3880

Abstract

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. Abstract : To B or not to B : This Minireview describes recent advances (2017–2019) in the catalytic hydroboration of N‐heteroarenes. A diverse range of new catalytic systems including the homogeneous and heterogeneous systems, and the metal‐ and metal‐free precatalysts, are described with a strong emphasis on their unique hydride transfer pathways bringing about breakage of N‐aromaticity, which are closely related to chemo‐, regio‐ and stereooutcomes observed in the catalyzed hydroboration.