Gold‐catalyzed Intermolecular Oxidations of 2‐Ketonyl‐1‐ethynyl Benzenes with N‐Hydoxyanilines to Yield 2‐Aminoindenones via Gold Carbene Intermediates

Mokar, Bhanudas Dattatray; Huple, Deepak B.; Liu, Rai‐Shung

doi:10.1002/ange.201606467

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Angewandte Chemie

2016

DOI: 10.1002/ange.201606467

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Gold‐catalyzed Intermolecular Oxidations of 2‐Ketonyl‐1‐ethynyl Benzenes with N‐Hydoxyanilines to Yield 2‐Aminoindenones via Gold Carbene Intermediates

Bhanudas Dattatray Mokar

Deepak B. Huple

Rai‐Shung Liu

Abstract: Gold‐catalyzed oxidations of 2‐ketonyl‐1‐ethynyl benzenes with N‐hydroxyanilines yield 2‐aminoindenone derivatives efficiently. Experimental data suggests that this process involves an α‐oxo gold carbene intermediate, generated from the attack of N‐hydroxyaniline on furylgold carbene intermediate, rather than the typical attack of oxidants on π‐alkynes.

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Cited by 5 publications

References 64 publications

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An Unusual Conversion of 2‐(Alkynonyl)Alkynylbenzenes to Isocoumarins by a Retro‐Favorskii‐like Degradation

Santhi

Baire

2019

Chemistry An Asian Journal

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We report the discovery of an anomalous reaction of 2‐(alkynonyl)alkynylbenzenes under AgI catalysis for the selective formation of isocoumarins. This reaction is previously undocumented for 2‐(alkynonyl)alkynylbenzenes in terms of the reaction mechanism and the product formed. Water (H2O18) labeling studies suggested a possible mechanistic pathway in which the initial formation of a pyrylium ion is followed by hydrative dealkynylation, that is, water incorporation and alkyne expulsion, similar to a retro‐Favorskii reaction.

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An Unusual Conversion of 2‐(Alkynonyl)Alkynylbenzenes to Isocoumarins by a Retro‐Favorskii‐like Degradation

Santhi

Baire

2019

Chemistry An Asian Journal

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Gold‐Catalyzed Annulations of N‐Propargyl Ynamides with Anthranils with Two Distinct Chemoselectivities

Hsu

Hsieh

Liu

2019

Chemistry A European J

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Gold‐catalyzed annulation of N‐propargyl ynamides with anthranils can proceed by two distinct mechanisms. In the case of a terminal N‐propargyl ynamide, its resulting α‐imino gold carbene reacts with a tethered alkyne to generate a vinyl cation to enable hydrolysis, which ultimately yields a pyrrolo[2,3‐b]quinoline derivative after treatment with p‐toluenesulfonic acid. For an internal alkyne, its α‐imino gold carbene reacts with a tethered alkyne via either a vinyl cation or an alkenylgold carbene; both paths ultimately lead to a 4‐ketone‐2‐aminopyrrole derivative. Our mechanistic analysis indicates that water is a better nucleophile than anthranil for terminal ynamides, whereas water and anthranils are equally reactive for internal ynamides.

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Gold‐Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)‐Additions and 1,2‐Carbon Migration

Skaria

Kuo

et al. 2020

Chemistry A European J

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This work reports gold‐catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E‐configured α‐amino‐2‐en‐1‐ones and ‐1‐als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)‐nucleophilic additions on terminal alkynes, in contrast to a typical C(2)‐route. For 3,3‐dialkylprop‐1‐yn‐3‐ols, a methyl substituent is superior to long alkyl chains as the 1,2‐migration groups toward α‐imino gold carbenes. For secondary prop‐1‐yn‐3‐ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)‐regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.

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Gold‐catalyzed Intermolecular Oxidations of 2‐Ketonyl‐1‐ethynyl Benzenes with N‐Hydoxyanilines to Yield 2‐Aminoindenones via Gold Carbene Intermediates

Cited by 5 publications

References 64 publications

An Unusual Conversion of 2‐(Alkynonyl)Alkynylbenzenes to Isocoumarins by a Retro‐Favorskii‐like Degradation

An Unusual Conversion of 2‐(Alkynonyl)Alkynylbenzenes to Isocoumarins by a Retro‐Favorskii‐like Degradation

Gold‐Catalyzed Annulations of N‐Propargyl Ynamides with Anthranils with Two Distinct Chemoselectivities

Gold‐Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)‐Additions and 1,2‐Carbon Migration

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