Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions

Singh, Rahulkumar Rajmani; Liu, Rai‐Shung

doi:10.1039/c7cc01304c

Cited by 37 publications

(20 citation statements)

References 65 publications

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“…Thus, the arenediazonium salts-triggered radical chain propagation pathway is less likely. [45][46][47] Scheme 7. Stoichiometric mechanistic study.…”

Section: Angewandte Chemiementioning

confidence: 99%

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

et al. 2018

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Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp 2and sp 3 -hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative CÀX (heteroatom) and CÀC couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy) 3 Cl 2 dual catalysis. Scheme 1. Strategies for the synthesis of biarylboronates.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…Thus, the arenediazonium salts-triggered radical chain propagation pathway is less likely. [45][46][47] Scheme 7. Stoichiometric mechanistic study.…”

Section: Angewandte Chemiementioning

confidence: 99%

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

et al. 2018

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“…For example, Tayama, Xu and Yang have reported the C(sp 2 )–H insertion reaction of α‐aryl‐α‐diazoesters with one equivalent of N , N ‐disubstituted aniline only to afford single C(sp 2 )–H insertion product (Scheme a). The double additions of the diazo compound with two nucleophiles have rarely been reported . For example, Liu reported the oxidative couplings reactions of aryl diazo cyanide with two molecules of indoles to afford bis(indolyl)methane derivatives; therein, an attempt for controlling the reaction with one molecule of indole was unsuccessful (Scheme b) .…”

Section: Introductionmentioning

confidence: 89%

“…The double additions of the diazo compound with two nucleophiles have rarely been reported . For example, Liu reported the oxidative couplings reactions of aryl diazo cyanide with two molecules of indoles to afford bis(indolyl)methane derivatives; therein, an attempt for controlling the reaction with one molecule of indole was unsuccessful (Scheme b) . In addition, many achievements on the cyclopropanation of diazo compounds with olefins have been accomplished .…”

Section: Introductionmentioning

confidence: 89%

Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines

et al. 2019

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On the basis of a tandem strategy, AgSbF6/Rh2(OAc)4/Ag3PO4‐mediated reaction of 2‐diazo‐3,5‐dioxo‐6‐ynoate (ynones) with N,N‐disubstituted anilines or aza‐aromatic hydrocarbons afforded a series of 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones) and 2‐(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates (or ketones). For N‐allyl‐N‐substituted aniline, the corresponding cyclopropanation did not occurred. Disymmetric 2,2‐bis(4‐aminoaryl or aza‐aryl)‐2‐(4‐pyranonyl)acetates were also obtained in good yield from 2‐(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates and N,N‐disubstituted anilines (or aza‐aromatic hydrocarbons) by C(sp3)–C(sp2) cross‐coupling reaction. AgSbF6/Ag3PO4 plays a key role in the C(sp3)–C(sp2) cross‐coupling reaction. This unique synthetic method for synthesis of two desired products starting from identical materials was proved to be efficient except for N‐substituted aniline.

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“…In addition, the reaction needs continuous irradiation, and no conversion was observed without light. Thus, the arenediazonium salts‐triggered radical chain propagation pathway is less likely …”

Section: Methodsmentioning

confidence: 99%

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

et al. 2018

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Organoboron compounds are versatile synthetic building blocks.W eh erein report an ew strategy,aphotochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts,w hichi s orthogonal to common strategies and therefore au nique tool for synthesis of valuable biarylboronates.W ith this new methodology aw ide array of diversely functionalizeds p 2and sp 3 -hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis,a llows for one-pot iterative CÀX (heteroatom) and CÀCc ouplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy) 3 Cl 2 dual catalysis.Scheme 1. Strategies for the synthesis of biarylboronates.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

show abstract

Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions

Cited by 37 publications

References 65 publications

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Selective Synthesis of 2‐(4‐Aminoaryl)‐2‐(4‐pyranonyl)acetates and 2,2‐Bis(4‐aminoaryl)‐2‐(4‐pyranonyl)acetates from 2‐Diazo‐3,5‐dioxo‐6‐ynoates (ynones) and Aromatic Amines

Light‐Induced Gold‐Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

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