Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Yue, Fuyang; Dong, Jianyang; Liu, Yuxiu; Wang, Qingmin

doi:10.1021/acs.orglett.1c00399

Cited by 37 publications

(46 citation statements)

References 49 publications

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“…presented a different approach to form alkyl radicals from boronic acids (Scheme 20). [48] In this case, they observed through quenching experiments that benzensulfinates are able to activate boronic acids towards single‐electron oxidation. Following the pathway of a redox‐neutral elimination, the authors found broad applicability of the reaction conditions, that could be applied to variously substituted benzensulfinates and to primary and secondary alkyl boronic acids.…”

Section: Radical Generation Through a Reductive Quenching Cyclementioning

confidence: 99%

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions

et al. 2022

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The chemistry of boron compounds has been profoundly investigated in the last decades, leading to ubiquity in many synthetic applications as well as biologically active molecules. Since the advent of photoredox catalysis, an upsurge in the discovery of suitable radical precursors has been witnessed, and boron is becoming a protagonist in this field. Despite many studies focused on trifluoroborates, the use of boronic acids and esters have received much less attention in this regard. Because of their high oxidation potential, the development of methods to enable their involvement in photocatalyzed reactions is only recent. Nonetheless, this review summarizes novel strategies developed to unlock their role as radical precursors in photochemical reactions and discloses the potential that boronic acids and esters own, when their intrinsic chemical properties are exploited.

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Section: Radical Generation Through a Reductive Quenching Cyclementioning

confidence: 99%

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions

et al. 2022

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“…Alkyl boronic acids could not efficiently quench excited-state photocatalysts to generate the corresponding alkyl radicals because of their high oxidation potentials ( E red = +2.5 V vs SCE). In 2021, Wang and co-workers overcame this problem by using benzenesulfinate as an alternative Lewis base, which was in situ generated from alkenyl sulfones in the reaction course, to decrease the oxidation potentials of boronic acids (Scheme D) . This protocol permitted the alkenylation reactions of a wide array of boronic acids directly, without the need for the preparation of potassium α-pyrrolidinyltrifluoroborates.…”

Section: Radical-mediated Desulfonylation Of Sulfones Via C–s Bond Cl...mentioning

confidence: 99%

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

et al. 2021

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As the "chemical chameleon", sulfonyl-containing compounds and their variants have been merged with various types of reactions for the efficient construction of diverse molecular architectures by taking advantage of their incredible reactive flexibility. Currently, their involvement in radical transformations, in which the sulfonyl group typically acts as a leaving group via selective C−S, N−S, O−S, S−S, and Se−S bond cleavage/ functionalization, has facilitated new bond formation strategies which are complementary to classical two-electron cross-couplings via organometallic or ionic intermediates. Considering the great influence and synthetic potential of these novel avenues, we summarize recent advances in this rapidly expanding area by discussing the reaction designs, substrate scopes, mechanistic studies, and their limitations, outlining the state-of-the-art processes involved in radical-mediated desulfonylation and related transformations. With a specific emphasis on their synthetic applications, we believe this review will be useful for medicinal and synthetic organic chemists who are interested in radical chemistry and radical-mediated desulfonylation in particular. CONTENTS

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“…The process does not require the presence of an external Lewis base but utilizes the sulfinate anion by reduction of the expelled phenylsulfonyl radical by the reduced form of the photocatalyst (Scheme 13). 46…”

Section: Alkylboron Derivativesmentioning

confidence: 99%

Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization

2022

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Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Cited by 37 publications

References 49 publications

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions

Uncovering the Potential of Boronic Acid and Derivatives as Radical Source in Photo(electro)chemical Reactions

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization

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