I<sub>2</sub>-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

Fan, Wei; Yang, Zhen; Jiang, Bo; Li, Guigen

doi:10.1039/c6qo00851h

Cited by 21 publications

(8 citation statements)

References 47 publications

(21 reference statements)

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“…In 2017, Li and co‐workers reported an iodine‐promoted intermolecular C(sp 2 )−S bond coupling for the synthesis of 3‐thiolated indoles and pyrroles under microwave irradiation, with triethylammonium thiolates as the reliable sulfenylating reagents (Scheme 34). [88] Under standard conditions, various C,S‐tethered bisindoles 103 and pyrrole‐indole pairs 105 were obtained in relatively good yields. In the control experiments, no obvious change of the reaction was observed in the presence of TEMPO or BHT, which suggested that no radical process was involved in this transformation.…”

Section: Iodine‐promoted C−s Bonds Formationmentioning

confidence: 99%

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Zhang

Wang

Jiang

et al. 2020

Chemistry A European J

106

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Sulfur-containing scaffold, as aubiquitous structural motif, has been frequently used in natural products, bioactive chemicals and pharmaceuticals, particularly CÀS/NÀS bonds are indispensable in many biological importantc ompounds and pharmaceuticals. Development of mild and general methods for CÀS/NÀSb onds formation hasg reat significance in modern research. Iodine and its derivativesh ave been recognizeda si nexpensive,e nvironmentally benign and easy-handled catalysts or reagents to promote the construction of CÀS/NÀSb onds under mild reactionc onditions, with good regioselectivities andb road substrate scope.E specially based on this, severaln ew strategies, such as oxidation relay strategy,havebeen greatlydeveloped and accelerated the advancement of this field. This review focuses on recent advances in iodine and its derivatives promoted hybridized CÀS/NÀSbonds formation.The features and mechanisms of corresponding reactions are summarized and the results of some cases are compared with those of previous reports. In addition, the future of this domain is discussed.

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Section: Iodine‐promoted C−s Bonds Formationmentioning

confidence: 99%

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Zhang

Wang

Jiang

et al. 2020

Chemistry A European J

106

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“…In 2017, Li and Jiang group, discussed easily acessible triethylammonium thiolates as new and ecologically sound sulfenylating agents for well‐planned and experimental metal‐free and microwave assisted preparation of sulfenylated pyrroles with moderate to fabulous yields (Scheme 129). [146] …”

Section: C−h Functionalization Of Pyrrolesmentioning

confidence: 99%

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Hunjan

Panday

Gupta

et al. 2021

The Chemical Record

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Among the known aromatic nitrogen heterocycles, pyrrole represents a privileged aromatic heterocycle ranging its occurrence in the key component of “pigments of life” to biologically active natural products to active pharmaceuticals. Pyrrole being an electron‐rich heteroaromatic compound, its predominant functionalization is legendary to aromatic electrophilic substitution reactions. Although a few excellent reviews on the functionalization of pyrroles including the reports by Baltazzi in 1963, Casiraghi and Rassu in 1995, and Banwell in 2006 are available, they are fragmentary and over fifteen years old, and do not cover the modern aspects of catalysis. A review covering a comprehensive package of direct functionalization on pyrroles via catalytic and non‐catalytic methods including their translational potential is described. Subsequent to statutory yet concise introduction, the classical functionalization on pyrroles using Lewis acids largely following an ionic mechanism is discussed. The subsequent discussion follows the various metal‐catalyzed C−H functionalization on pyrroles, which are otherwise difficult to implement by Lewis acids. A major emphasize is given on the radical based pyrrole functionalization under metal‐free oxidative conditions, which is otherwise poorly highlighted in the literature. Towards the end, the current development of pyrrole functionalization under photocatalyzed and electrochemical conditions is appended. Only a selected examples of substrates and important mechanisms are discussed for different methods highlighting their scopes and limitations. The aromatic nucleophillic substitution on pyrroles (being an electron‐rich heterocycle) happened to be the subject of recent investigations, which has also been covered accentuating their underlying conceptual development. Despite great achievements over the past several years in these areas, many challenges and problems are yet to be solved, which are all discussed in summary and outlook.

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“…Synthesis of 3‐sulfenyl indoles from indoles and thiols with the use of the I 2 /DMSO system was carried out in DCE at 60 °C and provided sulfenylated products in 67–96 % yields [20] . The same system was applied for the sulfenylation of indoles at the 3 d position with triethylammonium thiolates under microwave irradiation [21] . The I 2 /H 2 O 2 system was also proposed for the synthesis of 3‐sulfenyl indoles [22] .…”

Section: Thiols As Sulfenylating Agentsmentioning

confidence: 99%

Sulfenylation of Indoles Mediated by Iodine and Its Compounds

2021

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Indole represents one of the most common and important heterocyclic scaffolds omnipresent in a plenty of natural products and medicinal agents. Development of the synthetic routes to 3‐substituted indoles attracts a considerable attention due to a huge amount of biologically relevant molecules containing 3‐substituted indole moiety. Reactions of indoles halogenation, nitration, acylation, and alkylation at the 3d position have been known for several decades and continue developing now. Processes of indoles sulfenylation are much less studied. However, 3‐sulfenylated derivatives possess promising biological properties. This review summarizes nearly 100 references from the middle of the 20th century to 2021, concerning reactions of indoles sulfenylation mediated by iodine and its compounds. The manuscript is divided into the sections according to the classes of compounds used as sulfenylating agents.

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I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

Cited by 21 publications

References 47 publications

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Sulfenylation of Indoles Mediated by Iodine and Its Compounds

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I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

Cited by 21 publications

References 47 publications

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Recent Advances in Iodine‐Promoted C−S/N−S Bonds Formation

Recent Advances in Functionalization of Pyrroles and their Translational Potential

Sulfenylation of Indoles Mediated by Iodine and Its Compounds

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Product

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I₂-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents