Gold(I)‐Catalyzed Carbothiolation via Rearrangement of S‐Propargyl Group: An Access to 3‐Allenyl or 3‐Indenyl Benzo[<i>b</i>]thiophenes

Enolates formed from 1‐phenyl‐5‐tetrazolyl β‐ketosulfones containing a tetrasubstituted α carbon centre undergo elimination to allenes with up to four substituents at the cumulene unit when treated with a weak base (phenolate) in DMSO at room temperature. The reaction is completely regioselective for allene vs diene formation in nearly all investigated cases and it proceeds with central‐to‐axial chirality transfer.

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Stereospecific Synthesis of Allenes from β‐Ketosulfones

Wasilewska-Rosa

Kisiel

Tkaczyk

et al. 2023

Adv Synth Catal

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One‐Pot Synthesis of 2‐Aminothiophenes by Au(I)‐Catalyzed Cascade Reaction Including Hydrothiolation, Thio‐Claisen Rearrangement, and Cycloisomerization

Oonishi,

Ueda,

Sato

2024

Adv Synth Catal

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The cascade reaction of ynamides with propargyl thiols by Au(I) catalysis involving regioselective hydrothiolation, thio‐Claisen rearrangement, and cycloisomerization to generate 2‐aminothiophenes in a one‐pot manner is described. In this reaction, the selection of reaction temperature is crucial, with the initial step, namely hydrothiolation, conducted at a low temperature (40°C), followed by the subsequent reaction requiring an increase in temperature (>110°C). Furthermore, it was revealed that multi‐substituted anilines could be synthesized efficiently from the resulting 2‐aminothiophenes.

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Developments in the Construction of Benzo[b]Thiophenes from 2‐Alkynylthioanisoles by Electrophilic and Radical Cyclization Reactions

Shang,

Ma,

Xie

et al. 2024

Eur J Org Chem

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Benzo[b]thiophene moieties are important skeletons which have been widely found in many natural products, pharmaceuticals, as well as functionalized materials. 2‐Alkynylthioanisoles, a class of bifunctional compounds bearing methylthio and alkynyl groups, are easily accessible from Pd‐catalyzed Sonogashira coupling between 2‐halothioanisoles and terminal alkynes, which have been widely employed as synthons in the construction of benzo[b]thiophenes through an electrophilic or a radical pathway. This review summarizes the related developments with a particular focus on the reaction mechanism. We hope it will help in future research in this area and believe that with the discovery of new catalytic systems, the industrial synthesis of benzo[b]thiophenes from 2‐alkynylthioanisoles will be achieved soon.

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Gold(I)‐Catalyzed Carbothiolation via Rearrangement of S‐Propargyl Group: An Access to 3‐Allenyl or 3‐Indenyl Benzo[b]thiophenes

Cited by 4 publications

References 34 publications

Stereospecific Synthesis of Allenes from β‐Ketosulfones

Stereospecific Synthesis of Allenes from β‐Ketosulfones

One‐Pot Synthesis of 2‐Aminothiophenes by Au(I)‐Catalyzed Cascade Reaction Including Hydrothiolation, Thio‐Claisen Rearrangement, and Cycloisomerization

Developments in the Construction of Benzo[b]Thiophenes from 2‐Alkynylthioanisoles by Electrophilic and Radical Cyclization Reactions

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