ArticleJournal of the American Chemical Society2016
Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Metal-Free Electrophilic Borylative Cyclizations of Alkynes.Chemical record (New York, N.Y.) · 2026Review
- Synthesis and Fluorescent Properties of Alkynylated 3‑Methylidenephthalides with Extended π‑Systems.ACS omega · 2025Article
- Stereoselective Control of the Cu Activation of β,β-Diboryl Acrylates for Allylic Coupling Protocols with Concomitant Lactonization.Organic letters · 2024Article
- Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids.Molecules (Basel, Switzerland) · 2023Article
- Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade.Beilstein journal of organic chemistry · 2023Article
- Metal-Free Temperature-Controlled Regiodivergent Borylative Cyclizations of Enynes: BClAngewandte Chemie (International ed. in English) · 2022Article
- Emergence of 2-Pyrone and Its Derivatives, from Synthesis to Biological Perspective: An Overview and Current Status.Topics in current chemistry (Cham) · 2021Review
- Organophosphorus-catalyzed relay oxidation of H-Bpin: electrophilic C-H borylation of heteroarenes.Chemical science · 2020Article
- Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds.Angewandte Chemie (International ed. in English) · 2020Article
- Carbometalation and Heterometalation of Carbon-Carbon Multiple-Bonds Using Group-13 Heavy Metals: Carbogallation, Carboindation, Heterogallation, and Heteroindation.Chemistry, an Asian journal · 2020Review
- B(CChemical science · 2019Article
- Selective oxymetalation of terminal alkynesChemical science · 2018Article
- Divergent Elementoboration: 1,3-Haloboration versus 1,1-Carboboration of Propargyl Esters.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- Reactions of biologically inspired hydride sources with B(CPhilosophical transactions. Series A, Mathematical, physical, and engineering sciences · 2017Article
- Mechanistic Studies of Formal Thioboration Reactions of Alkynes.The Journal of organic chemistry · 2017Article
- Diversification reactions of γ-silyl allenyl esters: selective conversion to all-carbon quaternary centers and γ-allene dicarbinols.Chemical communications (Cambridge, England) · 2017Article
- BClAngewandte Chemie (International ed. in English) · 2017Article
- Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes.Angewandte Chemie (International ed. in English) · 2016Article
- Single-Flask Multicomponent Synthesis of Highly Substituted α-Pyrones via a Sequential Enolate Arylation and Alkenylation Strategy.Organic letters · 2016Article
- Contrasting Frustrated Lewis Pair Reactivity with Selenium- and Boron-Based Lewis Acids.Angewandte Chemie (International ed. in English) · 2016Article
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4 authors.
Funding
Abstract
A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organoboron building blocks for downstream functionalization. This method has functional group compatibility, is scalable, and proceeds with readily available materials: B-chlorocatecholborane and methyl esters. Mechanistic studies indicate that the B-chlorocatecholborane acts as a carbophilic Lewis acid toward the alkyne, providing a mechanistically distinct pathway for oxyboration that avoids B-O σ bond formation and enables this catalyst-free route.
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