A novel stereoselective synthesis of (<i>Z</i>)‐α‐arylsulfanyl‐α,β‐unsaturated ketones via Stille coupling of (<i>E</i>)‐α‐arylsulfanylvinylstannanes with acyl halides

Yao, Fang; You, Shengyong; Cai, Mingzhong

doi:10.1002/hc.20536

Cited by 4 publications

(2 citation statements)

References 39 publications

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“…Some ( Z )‐α‐SAr‐chalcones were synthesized through the Stille coupling of ( E )‐α‐arylsulfanylvinylstannanes with acyl halides in the presence of Pd(PPh 3 ) 4 catalyst and CuI cocatalyst as shown in Figure 39 [155] . Later, the same ( Z )‐α‐SAr‐chalcones were prepared by a one‐pot reaction that involved palladium catalyzed hydrostannylation of acetylenic sulfides with tribytylin hydride (Bu 3 SnH) followed by Stille coupling with acyl chloride [156] …”

Section: Different α‐Substituted Chalconesmentioning

confidence: 99%

α‐Substituted Chalcones: A Key Review

Al-Rifai

Mubarak

2021

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Chalcones are attractive chemical motifs with various biological activities. Aryl substituted chalcones have been extensively studied and reviewed through the years. However, α‐substituted chalcones have rarely been investigated. Hence, this review highlights the α‐substituted chalcones: their synthetic routes, reported biological activities, and transformations to other organic compounds. To the best of our knowledge, this would be the first comprehensive review about α‐substituted chalcones. α‐Substitution of chalcones represents a promising approach to tune their reactivity since it has a direct influence on their activity as Michael acceptors. Additionally, α‐substitution has its effect on the structure and conformation of chalcones. Altering the reactivity of chalcones by α‐substitution has a great impact on their biological activity.

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Section: Different α‐Substituted Chalconesmentioning

confidence: 99%

α‐Substituted Chalcones: A Key Review

Al-Rifai

Mubarak

2021

ChemistrySelect

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“…However, the Stille coupling reaction of the intermediates 2 with aliphatic acyl chlorides did not occur under the same conditions perhaps due to the presence of the steric barrier from α-aryl groups. It was reported that the Stille coupling reactions of sterically hindered (E)-α-selanyl-vinylstannanes, 20 (E)-α-arylsulfonylvinylstannanes 21 and (E)-α-arylthiovinylstannanes 22 with aliphatic acyl chlorides was also unsuccessful.…”

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confidence: 99%