ArticleNature communications2023
Direct nucleophilic and electrophilic activation of alcohols using a unified boron-based organocatalyst scaffold.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
What it found
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Who cites it
4 citing papers in PubMed.
- Tryptophan Bioconjugation through Auxiliary Boron-Accelerated, Additive-Free Friedel-Crafts Alkylation.JACS Au · 2026Article
- Scandium-Catalyzed Highly Selective Deoxygenation of Alcohols by Using Hydrosilanes as Reductants.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Designing Functional and Responsive Molecules with Boronic Acids.Accounts of chemical research · 2025Article
- Modular Synthesis of Complex Benzoxaboraheterocycles through Chelation-Assisted Rh-Catalyzed [2 + 2 + 2] Cycloaddition.ACS catalysis · 2024Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Organocatalytic strategies for the direct activation of hydroxy-containing compounds have paled in comparison to those applicable to carbonyl compounds. To this end, boronic acids have emerged as valuable catalysts for the functionalization of hydroxy groups in a mild and selective fashion. Distinct modes of activation in boronic acid-catalyzed transformations are often accomplished by vastly different catalytic species, complicating the design of broadly applicable catalyst classes. Herein, we report the use of benzoxazaborine as a general scaffold for the development of structurally related yet mechanistically divergent catalysts for the direct nucleophilic and electrophilic activation of alcohols under ambient conditions. The utility of these catalysts is demonstrated in the monophosphorylation of vicinal diols and the reductive deoxygenation of benzylic alcohols and ketones respectively. Mechanistic studies of both processes reveal the contrasting nature of key tetravalent boron intermediates in the two catalytic manifolds.
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Registered trials
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