Transition metal- and light-free radical borylation of alkyl bromides and iodides using silane

Sun, Beiqi; Zheng, Sihan; Mo, Fanyang

doi:10.1039/d1cc02134f

Cited by 14 publications

(8 citation statements)

References 37 publications

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“…Chemicals were purchased from Accela, Acros, Adamas, Alfa Aesar, Bidepharm, Energy Chemical, Macklin, Leyan, and TCI and used as received. Alkyl iodides 2d , 2i , and 2n were prepared according to literature procedures …”

Section: Methodsmentioning

confidence: 99%

Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides

Liao,

Tian,

Tian

2023

J. Org. Chem.

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An unprecedented reductive cross-coupling reaction of allylammonium salts with alkyl electrophiles has been established through C−N bond cleavage. A range of allylammonium bromides smoothly participated in the nickel-catalyzed zincmediated allyl−alkyl cross-electrophile coupling reaction with alkyl iodides, delivering structurally diverse alkene products in moderate to good yields with high linear selectivity. Preliminary mechanistic experiments are consistent with the formation of an alkyl radical from the alkyl iodide.

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Section: Methodsmentioning

confidence: 99%

Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides

Liao,

Tian,

Tian

2023

J. Org. Chem.

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“…In 2019, Jiao and co‐workers [76] reported a visible‐light induced radical borylation of alkyl bromides catalyzed by 4‐phenylpyridine, which features a broad substrate scope and a novel reaction mechanism (Scheme 47). Reaction between B 2 cat 2 and 4‐phenylpyridine in the presence of base produces a mixture of complexes 140 and 141 , which undergoes an S N 2 reaction with alkyl bromide to generate 142 .…”

Section: Borylation Of C−x Bondsmentioning

confidence: 99%

Transition‐Metal‐Free Radical Borylation Reactions

et al. 2023

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Dedication to Prof. Weisheng Tian on the occasion of his 70th birthdayOrganoboron compounds are versatile synthons in synthetic chemistry, materials science, and medicinal chemistry. The preparation of them often requires either reactive organometallic reagents or transition metals. In recent years, transition-metal-free borylation methodologies using radical chemistry for CÀ B bond formation have attracted much attention and developed rapidly, which circumvents the use of preformed organometallic reagents. Various successful ap-proaches from different radical precursors (such as carboxylic acids, amines and alcohols, which are abundant in nature) through either thermochemical, photochemical or electrochemical pathways have been developed. Therefore, in this review, we hope to provide an overview of recent advances in the discovery, development, and mechanistic study of transitionmetal-free radical borylation processes. Borylation of CÀ N BondsAmines are cheap, widely commercially available, and are abundant in drugs and natural products. Thus, transforming readily available amines and amine derivatives into valuable boronic esters will be of great use.

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“…[1][2][3][4] Besides transition metal catalyzed borylation of organic compounds, metal free reactions with boryl reagents have attracted more and more attention in recent years, in particular the direct coupling of precursors with diboron esters. [5][6][7] The empty orbital of a boron atom can coordinate with atoms possessing lone pair electrons at the orbitals in a Lewis base, thus forming an electron donor-acceptor (EDA) pair and facilitating the cleavage of the B-B bond to induce radical reactions. 8 In the past decades, many strategies have been developed to generate various boryl radicals.…”

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confidence: 99%

Visible light induced boryl radical and its application in reduction of unsaturated XO (X = C, N, S) bonds

et al. 2023

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Transition metal- and light-free radical borylation of alkyl bromides and iodides using silane

Abstract: We report an operationally simple and neutral conditions for borylation of alkyl bromides and iodides to alkyl boronic esters under transition metal- and photo-free conditions. A series of substrates with...

Cited by 14 publications

References 37 publications

Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides

Nickel-Catalyzed Reductive Cross-Coupling of Allylammonium Salts with Alkyl Iodides

Transition‐Metal‐Free Radical Borylation Reactions

Visible light induced boryl radical and its application in reduction of unsaturated XO (X = C, N, S) bonds

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