Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates

Lockner, Jonathan W.; Dixon, Darryl D.; Risgaard, Rune; Baran, Phil S.

doi:10.1021/ol2023505

Cited by 180 publications

(87 citation statements)

References 56 publications

(28 reference statements)

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“…35 A year later, they demonstrated an intramolecular variant that could utilize either boronic acids or trifluoroborates (Figure 15). 36 Utilizing quinones as radicophiles, the Baran group were able to perform a radical/radical domino reaction to yield 100 . In this process, Ag(II) is generated via a persulfate-mediated single electron oxidation.…”

Section: Transition Metal-mediated Domino Reactionsmentioning

confidence: 99%

Catalytic Radical Domino Reactions in Organic Synthesis

2014

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Catalytic radical-based domino reactions represent important advances in synthetic organic chemistry. Their development benefits synthesis by providing atom- and step-economical methods to complex molecules. Intricate combinations of radical, cationic, anionic, oxidative/reductive, and transition metal mechanistic steps result in cyclizations, additions, fragmentations, ring-expansions, and rearrangements. This Perspective summarizes recent developments in the field of catalytic domino processes.

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Section: Transition Metal-mediated Domino Reactionsmentioning

confidence: 99%

Catalytic Radical Domino Reactions in Organic Synthesis

2014

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“…[4] Though it is a milder protocol, unfortunately the reaction is limited to only aliphatic nucleophiles. [8] In this context, the synthesis of such Het-Ar and Quin-Ar compounds by iron catalysis is desirable because of the environmental benignity, low cost, and availability of iron. [8] In this context, the synthesis of such Het-Ar and Quin-Ar compounds by iron catalysis is desirable because of the environmental benignity, low cost, and availability of iron.…”

Section: Introductionmentioning

confidence: 99%

Iron‐Catalyzed Direct C–H Arylation of Heterocycles and Quinones with Arylboronic Acids

Deb¹,

Manna²,

Maji³

et al. 2013

Eur J Org Chem

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The arylation of C–H bonds to generate heteroaryl–aryl (Het–Ar) and arylated quinone (Quin–Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het–Ar and Quin–Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic amounts of inexpensive Fe(NO3)3. The C‐arylated quinone compounds can be prepared by reacting arylboronic acids with either quinone or hydroquinone. The present method is operationally simple, scalable, does not require prefunctionalization of the heterocycle or quinone, and can tolerate a wide variety of functional groups in the coupling partners. These qualities are expected to render this method attractive for academic and industrial use.

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“…Encouragement in this regard was found in the work of Sanford and Glorius, who had demonstrated that cooperative catalysis between transition metals and photoredox catalysts is indeed possible (15–17). Potassium organotrifluoroborates were identified as promising partners in this new class of cross-couplings, as previous reports have documented their ability to function as carbon radical sources upon single-electron oxidation (18, 19). Furthermore, Akita and co-workers have used Ir[dFCF 3 ppy] 2 (bpy)PF 6 (dFCF 3 ppy = 2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine; bpy = bipyridine) as a catalyst for the oxidation of activated potassium organotrifluoroborates, demonstrating the feasibility of their implementation in the proposed single-electron transmetalation manifold (20, 21).…”

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confidence: 99%

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis

Tellis

Primer

Molander

2014

Science

1,107

623

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The routine application of Csp3-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.

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Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates

Cited by 180 publications

References 56 publications

Catalytic Radical Domino Reactions in Organic Synthesis

Catalytic Radical Domino Reactions in Organic Synthesis

Iron‐Catalyzed Direct C–H Arylation of Heterocycles and Quinones with Arylboronic Acids

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis

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