A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

André‐Joyaux, Emy; Kuzovlev, Andrey; Tappin, Nicholas D. C.; Renaud, Philippe

doi:10.1002/ange.202004012

Cited by 10 publications

(2 citation statements)

References 77 publications

(85 reference statements)

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“…After one-carbon homologation of the alkyl Bpin of 4 with chloroiodomethane and n -BuLi, 11a protodeboronation of the alkylboronate ester in the presence of 4- tert -butylcatechol and MeOBcat catalyst led to the corresponding product 5 with a yield of 76% over two steps. 11b The protodeboronation of the alkenylboronate ester 3l was conducted in the presence of AgF, resulting in the formation of 6 in a yield of 71%. 9b Palladium-catalyzed Suzuki–Miyaura cross-coupling of 3l with bromobenzene or iodomethane provided ( E )-allyl fluorides 7 or 8 in good yields without any degradation of the E / Z ratios.…”

Section: Table 1 Reaction Optimization Amentioning

confidence: 99%

Chemo-, Regio-, and Stereoselective Access to (E)-Boryl-Substituted Allyl Fluorides via Electrophilic Fluorodesilylation

Jung¹,

Cho²

2023

Synlett

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Here, we report a transition-metal-free chemo-, regio-, and stereoselective electrophilic fluorodesilylation of α-silyl-substituted allylboronate esters. The α-silyl-substituted allylboronate esters can be chemoselectively coupled with selectfluor resulting in a variety of (E)-boryl-substituted allyl fluorides in good yields with γ- and (E)-selectivity. The utilities of the obtained (E)-boryl-substituted allyl fluorides are highlighted by further modifications to afford allyl or alkyl fluoride derivatives.

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Section: Table 1 Reaction Optimization Amentioning

confidence: 99%

Chemo-, Regio-, and Stereoselective Access to (E)-Boryl-Substituted Allyl Fluorides via Electrophilic Fluorodesilylation

Jung¹,

Cho²

2023

Synlett

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“…Such an approach involving the in situ transesterification of R-Bpin derivatives to R–Bcat derivatives was recently reported to perform radical reactions. 33 Various transesterification procedures were tested, and the results are summarized in Table 2 . The reactions were run at 70 °C in toluene for 24 hours.…”

Section: Table 1 Optimization Of the Cyclopropanation S...mentioning

confidence: 99%

Intramolecular Asymmetric Cyclopropanation Using Air-Stable Alkylboronic Esters

Vedani,

Gnägi-Lux,

Dénès

et al. 2023

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The preparation of polysubstituted bicyclo[3.1.0]hexanes starting from air-stable substituted pent-4-en-1-ylboronic acid esters has been investigated. The method involves a Matteson homologation with LiCHCl2, leading to 1-chlorohex-5-en-1-ylboronic acid ester intermediates. The subsequent intramolecular cyclopropanation step was performed in a one-pot process. With pinacol boronic esters, the cyclopropanation step was either performed thermally at 140 °C or at 70 °C after in situ transesterification to form a catechol boronic ester. This last approach is suitable for the preparation of enantioenriched bicyclo[3.1.0]hexanes using either chiral-auxiliary control or by taking advantage of the sparteine-controlled enantioselective boroalkylation of alcohols.

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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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A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

Cited by 10 publications

References 77 publications

Chemo-, Regio-, and Stereoselective Access to (E)-Boryl-Substituted Allyl Fluorides via Electrophilic Fluorodesilylation

Chemo-, Regio-, and Stereoselective Access to (E)-Boryl-Substituted Allyl Fluorides via Electrophilic Fluorodesilylation

Intramolecular Asymmetric Cyclopropanation Using Air-Stable Alkylboronic Esters

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

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