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              <i>t</i>
            </sup>BuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols

Pramanik, Milan; Mathuri, Ashis; Mal, Prasenjit

doi:10.1039/d2ob00079b

Cited by 4 publications

(1 citation statement)

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“…Radical addition to activated alkynes for cascade cyclization has become an important tool in organic synthesis. − Arylalkynoates are a particularly useful class of precursors for these reactions, as they can undergo regio- and stereocontrolled radical additions to produce highly substituted cyclic products with a high degree of structural complexity . Additionally, arylalkynoates can be easily synthesized from simple starting materials, making them readily accessible for use in organic synthesis .…”

Section: Introductionmentioning

confidence: 99%

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

et al. 2023

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Herein we report a cascaded chalcogenation of aryl alkynoates or N-arylpropynamides using 9-mesityl-10-methylacridinium perchlorate as a visible light photocatalyst to obtain selectively either 3sulfenylated/selenylated coumarins or spiro [4,5]trienones. In a radical initiated process, the spiro-cyclization reaction was favored due to the presence of a -OMe or -F substituent at the para position of the aryl group, which helped to stabilize the allylic radical intermediate formed during the reaction. Otherwise, 6-endo-trig cyclization led to 3-sulfenylated/selenylated coumarins. Overall, the new C−S/C−Se, C−C, and C�O bonds were formed in a single step. The Stern−Volmer quenching study, EPR experiments, light ON-OFF experiments, radical trapping experiments, etc., helped to understand the radical-based mechanism.

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Section: Introductionmentioning

confidence: 99%

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

et al. 2023

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Acid‐Promoted Carbon‐Carbon Triple Bond Cleavage of Ynones for the Synthesis of Benzo[d]oxazoles/Benzo[d]thiazoles and 1‐Arylethan‐1‐ones

Guo

et al. 2022

Eur J Org Chem

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A synchronous synthesis of benzo [d]oxazoles/benzo [d]thiazoles and 1-arylethan-1-ones enabled by acid-promoted CÀ C triple bond cleavage of ynones is disclosed. This reaction was accomplished with good tolerance of various functional groups and aminophenols/aminobenzenethiols to access the corre-sponding products, especially some structurally special 1arylethan-1-ones, in moderate to good yield. Furthermore, the readily accessible synthesis of some biologically active molecules has highlighted the synthetic utility of this strategy.

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Synthesis of dithioacetals via gold-catalysed hydrothiolation of vinyl sulfides

2023

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^tBuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols

Abstract: Selective radical addition to terminal alkynes is always a difficult task to achieve because it gives a mixture of stereo- and regioisomers. Herein we disclose the selective addition of aliphatic...

Cited by 4 publications

References 54 publications

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

Acid‐Promoted Carbon‐Carbon Triple Bond Cleavage of Ynones for the Synthesis of Benzo[d]oxazoles/Benzo[d]thiazoles and 1‐Arylethan‐1‐ones

Synthesis of dithioacetals via gold-catalysed hydrothiolation of vinyl sulfides

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t BuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols

Abstract: Selective radical addition to terminal alkynes is always a difficult task to achieve because it gives a mixture of stereo- and regioisomers. Herein we disclose the selective addition of aliphatic...

Cited by 4 publications

References 54 publications

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

Chemodivergent Chalcogenation of Aryl Alkynoates or N-Arylpropynamides Using 9-Mesityl-10-Methylacridinium Perchlorate Photocatalyst

Acid‐Promoted Carbon‐Carbon Triple Bond Cleavage of Ynones for the Synthesis of Benzo[d]oxazoles/Benzo[d]thiazoles and 1‐Arylethan‐1‐ones

Synthesis of dithioacetals via gold-catalysed hydrothiolation of vinyl sulfides

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^tBuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols