N‐Bromosuccinimide Promoted Direct Thiolation of Imidazoheteroaryl C‐H bonds with Disulfides

Maddi, Raghavender Reddy; Shirsat, Prashishkumar K.; Kumar, Santosh; Meshram, H. M.

doi:10.1002/slct.201601460

Cited by 17 publications

(8 citation statements)

References 39 publications

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“…Regioselective C‐3 sulfenylation of imidazo[1,2‐ a ]pyridines has been extensively explored until recently with hypervalent iodine reagents, [140–145] strong acidic conditions, [146] ionic liquids, [147] NCS ( N ‐chlorosuccinamide) [148] and NBS [149] . Very recently, Adimurthy et al [150] .…”

Section: Sulfenylationmentioning

confidence: 99%

“…[139] TBHP is proposed to dissociate into t-butoxide radical (43 A) and hydroxyl radical in presence of visible light followed by single electron transfer to afford t-butoxide radical (43 A) and hydroxide anion, which reacts further with benzenesulfinic acid (122) Regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines has been extensively explored until recently with hypervalent iodine reagents, [140][141][142][143][144][145] strong acidic conditions, [146] ionic liquids, [147] NCS (N-chlorosuccinamide) [148] and NBS. [149] Very recently, Adimurthy et al [150] reported a catalyst-free approach for C-3 sulfenylation of imidazo[1,2-a]pyridines. Continuing their efforts towards developing more enviornment viable methodologies, Rahaman and co-workers [151] have reported a metal-free, photocatalyst mediated, CDC protocol for the regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines (13) using thiols ( 9) as sulfenylating reagent.…”

Section: Visible Light Induced Sulfenylationmentioning

confidence: 99%

“…They prepared Katritzky salts (147) from different αamino acids (148) and reacted them with thiols (9) in presence of base (DIPEA) at room temperature under blue LED irradiation. The optimized reaction conditions was successfully applied for the synthesis of α-sulfenyl acid derivatives (149). Amino acid functionalisation by replacing amino group of αamino acids with thiols resulted into different functionalized thiols (149).…”

Section: Visible Light Induced Sulfenylationmentioning

confidence: 99%

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Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

et al. 2021

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Transition metal‐free sulfenylation of C−H bonds for C−S bond formation has recently emerged as sustainable protocols for the functionalisation of various molecules. Researchers have extensively developed such protocols for the construction of biologically relevant sulfur scaffolds. There has been a gradual shift from metal‐catalyzed to metal‐free C−S bond formation methodologies, because the latter offer environmentally benign and inherently safe access to novel synthetic routes in organic chemistry. The present review offers a dynamic discussion on recent advances in transition metal‐free C−S bond formation via C−H bond functionalization using different surrogate sulfenylating reagents. The review has comprehensively been devoted to radical and ionic mechanistic approaches. Some simple and eco‐friendly reagents for sulfenylation viz. tertbutyl hydrogen peroxide (TBHP), hydrogen peroxide (H2O2), iodine/potassium persulphate (I2/K2S2O8), inorganic bases, strong organic acids, iodine, I2/triphenyl phosphine (PPh3), N‐chlorosuccinamide (NCS), N‐bromosuccinamide (NBS), potassium iodate (KIO3), I2/bovine serum albumin (BSA), tetrabutyl ammonium iodide (TBAI)/HBr and graphene oxide along with their mechanistic approach has been detailed in this review. Moreover, modern methods for the C−S bond formation i. e., biocatalyst, electrochemical and visible light induced sulfenylation, and traditional sulfenylation methodologies have also been incorporated.

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Section: Sulfenylationmentioning

confidence: 99%

Section: Visible Light Induced Sulfenylationmentioning

confidence: 99%

Section: Visible Light Induced Sulfenylationmentioning

confidence: 99%

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Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

et al. 2021

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“…A plausible mechanism is illustrated in Scheme 17. Initially, disulfides 2 reacts with I 2 to generate an elecro In 2017, Meshram group [27] developed the N-bromosuccinimide promoted direct sulfenylation of imidazole-fused heterocycles with disulfides. A wide range of heterocycles and disulfides were tested, and the desired sulfenylated imidazo compounds were obtained in good to high yields in the presence of inexpensive NBS.…”

Section: Scheme 15 Sulfenylation Of Imidazo[15-a]quinolines With Dismentioning

confidence: 99%

Recent Progress in Transition Metal-Free C-Heteroatom Bond Formation by Functionalization of C-H Bond in Imidazole-Fused Heterocycles

Xu¹,

Chen²,

Wang³

2019

Chin. J. Org. Chem.

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Recently, the direct incorporation of heteroatom into imidazole-fused heterocycles through transition metal-free C-H functionalization has rapidly been advanced and become an eco-friendly synthetic tool for the synthesis of functionalized natural or bioactive molecules such as (hetero)arenes, olefins, carbonyl compounds. In particular, the C-H functionalization of imidazole-fused heterocycles has been considered to be the most important since it can lead to a new class of biologically active compounds. The recent progress in the incorporation of heteroatom into imidazole-fused heterocycles through transition metal-free C-H functionalization is introduced, and their mechanisms from a new perspective are also elaborated.

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“…18 Many elegant formylation processes have been developed for the sulfenylation at C3 of imidazo [1,2-a]pyridines. [19][20][21][22][23][24][25][26][27][28] However, there is no report on iron-catalyzed sulfenylation of imidazo[1,2-a]pyridine derivatives with thiols.…”

mentioning

confidence: 99%

Aerobic Iron(III)-Catalyzed Direct Thiolation of Imidazo[1,2-a]pyridine with Thiols

Qin

Weng³

et al. 2020

SynOpen

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A novel and efficient iron(III)-catalyzed regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines with thiols under oxygen atmosphere has been developed. The reaction proceeds in moderate to good yields with a broad range of substrates, providing a novel, efficient and green route for accessing synthetically useful C3-sulfenated imidazo-[1,2-a]pyridines. Moreover, the fluoride-containing C3-sulfenated imidazo-[1,2-a]pyridine 3ai exhibited superior anticancer activity and good safety profiles.

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N‐Bromosuccinimide Promoted Direct Thiolation of Imidazoheteroaryl C‐H bonds with Disulfides

Cited by 17 publications

References 39 publications

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

Recent Progress in Transition Metal-Free C-Heteroatom Bond Formation by Functionalization of C-H Bond in Imidazole-Fused Heterocycles

Aerobic Iron(III)-Catalyzed Direct Thiolation of Imidazo[1,2-a]pyridine with Thiols

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