Synthesis of (E)-iodo vinylsulfones via oxidative addition of thiol into alkyne under metal free condition

Synthesis of (E)‐β‐Iodovinyl Sulfones via Photoredox Catalyzed Difunctionalization of Terminal Alkynes

“…Thus, it becomes even more challenging where we may wish to install sulfone group without using any sulfonyl precursor, viz., utilizing thiols directly. To the best of our knowledge, the only report for the synthesis of β‐iodovinyl sulfones using thiols has been reported via coupling with alkynes utilizing iodine as halogenating source under reflux conditions [14] . Intriguingly, we could not come across any report that enables the synthesis of β‐iodovinyl sulfones at room temperatures.…”

“…To the best of our knowledge, the only report for the synthesis of β-iodovinyl sulfones using thiols has been reported via coupling with alkynes utilizing iodine as halogenating source under reflux conditions. [14] Intriguingly, we could not come across any report that enables the synthesis of β-iodovinyl sulfones at room temperatures. Thus, a mild and efficient approach employing readily available starting materials for the synthesis of βiodovinyl sulfone is highly desirable.…”

Advances in Vinyl Sulfone Catalyzed Synthesis: Methods, Mechanisms and Perspectives

“…The use of molecular iodine to promote the sulfonylation reaction for the synthesis of iodinevinyl sulfones is also a good option, which was proposed by Samanta and co‐workers in 2021 (Scheme 10). [60] They used inexpensive terminal alkynes such as aryl‐terminated acetylenes and alkyl‐terminated acetylenes and thiols as raw materials to obtain ( E )‐ β ‐iodovinyl sulfones by C−S bond coupling via H 2 O 2 oxidation. The process does not require the addition of transition metals and requires only the oxidant hydrogen peroxide with the promotion of molecular iodine, providing good yields and excellent regioselectivity and stereoselectivity, while easily enabling Gram‐grade synthesis.…”

“…Synthesis of vinyl sulfones mediated by I 2 . [60] Scheme 11. Synthesis of vinyl sulfones mediated by NaI.…”

A direct entry to polycyclic quinoxaline derivativesviaI2-DMSO mediated oxidative decarboxylation of α-amino acids and the subsequent Pictet–Spengler cyclization reaction

“…Though oxidative decarboxylation of α-amino acids is well documented, 23 molecular iodine is also used for this purpose. 24 Since we are very enthusiastic about discovering iodine-promoted organic transformations, 25 we wanted to examine the oxidative decarboxylation of amino acids under iodine catalyzed conditions and the subsequent Pictet–Spengler cyclization reaction for realizing various polycyclic quinoxaline derivatives. A large number of pyrrolo and indoloquinoxaline derivatives may be prepared under molecular iodine-mediated, metal-free conditions.…”