Single-Pot Access to Bisorganoborinates: Applications in Zweifel Olefination

Music, Arif; Baumann, Andreas N.; Spieß, Philipp; Hilgert, Nicolas; Köllen, Martin F.; Didier, Dorian

doi:10.1021/acs.orglett.9b00493

Cited by 12 publications

(9 citation statements)

References 46 publications

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“…Tributylcerium allowed for efficient halogen-cerium exchanges on aryl-and alkenyl-halides, and the resulting organocerium reagents were successfully engaged in Zweifel olefinations. 23 Gratifyingly, all the organometallics underwent stereospecific transformations, as shown in Scheme 2 (7a-c).…”

Section: Short Review Synthesismentioning

confidence: 99%

Forging C–C Bonds through Intramolecular Oxidative Coupling of Organoborates – An Overview

Didier¹

2022

Synthesis

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C-C bond formation has challenged the community of synthetic organic chemists for a few decades. Organoboron derivatives represent a mild and functional group tolerant class of reagents that can be handled without the need for inert conditions, being therefore adequate scaffolds for further studies towards the development of efficient methods that would increase the sustainability of current processes for coupling reactions. This short review summarizes the different approaches that have been developed to undergo C-C bond formation through intramolecular rearrangements of organoborate species.

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Section: Short Review Synthesismentioning

confidence: 99%

Forging C–C Bonds through Intramolecular Oxidative Coupling of Organoborates – An Overview

Didier¹

2022

Synthesis

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“…The whole reaction processes can be caried out in one pot and the organometallic reagents employed in the two steps can be permutated flexibly (Scheme 3 ). 4…”

Section: Zweifel Olefination With New Organometallic Speciesmentioning

confidence: 99%

Recent Progress on the Zweifel Olefination: An Update

Song,

2023

Synthesis

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During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. 1 Introduction 2 Zweifel Olefination with New Organometallic Species 3 Zweifel Olefination with New Migrating Groups 4 Electrochemical and Photocatalyzed Zweifel Olefination 5 New Elimination and Migration Patterns of Zweifel Olefination 6 Zweifel Olefination in Natural Product Synthesis 7 Other Reactions Involving the Zweifel Olefination Mechanism 8 Conclusions and Outlook

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“…Another convenient extension of the method was reported by the Didier Group in 2019, [40] in which preparation and isolation of the boronic ester previous to the Zweifel‐olefination is omitted. As shown in Scheme 12 aryl‐, hetereoaryl‐ or vinyl bromides are converted into vinyl lithium or vinyl magnesium species of type 33(i) , which are reacted with tri‐ n ‐butyl borate to 30(i) .…”

Section: Opening Small Heterocycles By 12‐rearrangementmentioning

confidence: 99%

Transition Metal Catalyst Free Synthesis of Olefins from Organoboron Derivatives**

Bojaryn

Hirschhäuser

2022

Chemistry A European J

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Stereoselective preparation of highly substituted olefins is still a severe challenge that requires well defined elimination precursors. Organoboron chemistry is particularly suited for the preparation of molecules with adjacent stereocenters. As organo boron substrates with leaving groups in β‐position can undergo stereospecific syn‐ or anti‐elimination, this chemistry harbors great potential for the synthesis of complex olefins. In recent years three main strategies emerged, which differ in their approach to the β‐functionalized organoboron elimination precursor. (i) Stereoselective preparation of such elimination precursor can be achieved by addition of a boron‐stabilized anion (d1) to an aldehyde or ketone (a1) or diastereoselective 1,3‐rearrangement of suitable boron‐ate‐complexes. Stereospecific methods rely either on (ii) diastereospecific 1,2‐metalate rearrangement of boron‐ate‐complexes that involve opening of appropriate heterocycles or (iii) addition of chiral carbenoids (d1*) to chiral boronates (a1*) with a leaving group in α‐position.

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Single-Pot Access to Bisorganoborinates: Applications in Zweifel Olefination

Cited by 12 publications

References 46 publications

Forging C–C Bonds through Intramolecular Oxidative Coupling of Organoborates – An Overview

Forging C–C Bonds through Intramolecular Oxidative Coupling of Organoborates – An Overview

Recent Progress on the Zweifel Olefination: An Update

Transition Metal Catalyst Free Synthesis of Olefins from Organoboron Derivatives**

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