Iodine-catalyzed allylic alkylation of sulfonamides and carbamates with allylic alcohols at room temperature

Wu, Wenhan; Rao, Weidong; Er, Ya Qin; Loh, Joanna K.; Poh, Chai Yun; Chan, Philip Wai Hong

doi:10.1016/j.tetlet.2008.02.079

Cited by 55 publications

(22 citation statements)

References 31 publications

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“…[65] Chan and co-workers applied I 2 as a catalyst in the nucleophilic addition of sulfonamides and carbamates to allylic alcohols. [66] The reaction is operationally straightforward and proceeds under very mild conditions with 5 mol-% of the catalyst at room temperature in good to excellent yields (up to 99 %). Duan and Wu described the efficient benzylation of dicarbonyl compounds by the reaction with I 2 operating in CH 3 NO 2 at 80°C.…”

Section: Iodinementioning

confidence: 99%

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

et al. 2010

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In 2005, the ACS Green Chemistry Institute (GCI) and the global pharmaceutical corporations developed the ACS GCI Pharmaceutical Roundtable to encourage the development of green chemistry and green engineering in the pharmaceutical industry. The Roundtable has established a list of key research areas including the direct nucleophilic reactions of alcohols. The substitution of activated alcohols is a frequently used approach for the preparation of active pharmaceutical ingredients. Alcohols are transformed into the reactive halides or sulfonate esters, thereby allowing their reaction with nucleophiles. Although the direct nucleophilic substitution of an alcohol should be an attractive process, as one of the byproducts from the reaction yields water, hydroxide is a poor leaving group that hinders the reaction. Recently, the direct substitution of allylic, benzylic, and tertiary alcohols has been achieved through an SN1 reaction with catalytic amounts of Brønsted or Lewis acids. In this review, the approaches leading to a greener process are examined in detail, and the advances achieved to date in this important transformation are presented.

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Section: Iodinementioning

confidence: 99%

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

et al. 2010

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“…The most important approaches are: (i) condensation of 2-aminopyridine with α-halocarbonyl compounds In recent years, Iodine has proved to be a very useful catalyst in carrying out synthesis of variety of heterocycles such as coumarins 22 , quinolines 23 , benzoxazoles 24 , benzimidazoles 25 and lactones 26 . Iodine has received increasing attention as an inexpensive, non-toxic and readily available catalyst for organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Puttaraju

Shivashankar

2013

RSC Adv.

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A facile and efficient protocol for the synthesis of novel imidazo[1,2-a]pyridines has been developed by one-pot reaction of aromatic aldehydes with 2-amino-5-chloropyridine and tertbutylisocyanide in the presence of I 2 in toluene at 70 °C . The present approach offers the advantages of simple methodology, clean, high atom-economy, mild condition, short reaction time, wide substrate scope, low environmental impact and high yield. Key WordsIodine, Imidazopyridines, Imidazo[1,2-a]pyridine, 2-aminopyridine, tert-butylisocyanide. IntroductionMulti-component synthesis have received considerable attention of organic chemists and emerged as a powerful tool for the construction of novel and complex molecular structures due to their advantages over conventional multistep synthesis. The major advantages of MCR's include low cost, shorter reaction times, high atom economy, energy saving and avoidance of time consuming and expensive protection, deprotection, isolation and purification process Result and discussionFirst the optimization of the reaction was studied for which the reaction of 2-chloropyridine-3-carbaldehyde, 5-chloro-pyridin-2-ylamine and tert-butylisocyanide was selected as a The role of solvents on the synthesis of imidazo[1,2-a]pyridine was then studied and the results are depicted (Table 2). Replacing the ethanol by chloroform produced the model in an A probable mechanistic pathway for the formation of imidazo[1,2-a]pyridine is outlined, ConclusionIn conclusion, a straightforward and efficient protocol for the one pot synthesis of Exprimental General informationThe melting points were determined by open capillary method using electric melting point apparatus and are uncorrected. The IR spectra (KBr disc) were recorded on a Shimadzu-8400SFT-IR Spectrophotometer.1 H NMR spectra were recorded on Bruker 300 MHz spectrometer and solution. The organic layer was separated and aqueous layer was extracted with ethyl acetate (15 ml X 3). The combined organic phase were washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude product which was purified on silica gel using hexane and ethyl acetate (7:3). 56.9, 104.5, 110.8, 117.3, 120.7, 121.3, 121.8, 123.2, 124.5, 126.0, 127.0, 128.6, 154.5 55.9, 117.8, 120.5, 121.7, 122.7, 125.7, 126.4, 131.1, 136.6, 140.7, 148.8, 149 3, 30.5, 56.8, 117.3, 119.9, 121.4, 122.8, 125.3, 125.6, 126.5, 132.3, 140.0, 140 C, 60.08: H, 5.67: N, 13.14: S, 10.02. Found: C, 59.91: H, 5.54: N, 13.01: S, 9.97. 0, 56.7, 109.8, 113.3, 117.5, 120.0, 120.7, 121.6, 124.7, 126.0, 130.8, 140.6, 151.8 56.7, 109.8, 113.3, 117.5, 120.0, 120.7, 121.6, 124.7, 126.0, 130.8, 140.6, 151.8 55, 57.31, 105.08, 114.07, 114.11, 117.26, 117.92, 121.14, 131.17, 140.89, 140.93, 145.86, 149.71, 150.56, 152.50 N-tert-butyl-6-chloro-2-(1H-imidazol-4-yl)H-imidazo[1,2-a]pyridin-3-amine (2g)

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“…Benzyl [172][173][174][175][176][177] , allyl 175,[178][179][180][181][182][183][184] and propargyl 175,185,186 alcohols 6 were treated with various nucleophiles in the presence of I 2 (2-20 mol%) and formed different types of products (Scheme 24, Table 20). Tertiary alcohols underwent elimination of water in the absence of nucleophiles providing the corresponding alkenes such as 59 (R 1 = R 2 = R 4 = H), in high yields (Scheme 24).…”

Section: Molecular Iodine-catalyzed Approachesmentioning

confidence: 99%

Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

Ajvazi¹,

Stavber²

2018

Arkivoc

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In recent years, nucleophilic substitution of alcohols leading to the formation of the C-C and C-heteroatom bonds has become an attractive process used in the synthesis of organic compounds, offering a potential impact on the environment, since water is the only by-product of the reaction. A comprehensive compilation of methods for the activation and displacement of a hydroxyl group covering the last seventeen years is the objective of the present review.

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Iodine-catalyzed allylic alkylation of sulfonamides and carbamates with allylic alcohols at room temperature

Cited by 55 publications

References 31 publications

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

Direct Nucleophilic S_N1‐Type Reactions of Alcohols

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

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Iodine-catalyzed allylic alkylation of sulfonamides and carbamates with allylic alcohols at room temperature

Cited by 55 publications

References 31 publications

Direct Nucleophilic SN1‐Type Reactions of Alcohols

Direct Nucleophilic SN1‐Type Reactions of Alcohols

Iodine-catalyzed three component reaction: a novel synthesis of 2-aryl-imidazo[1,2-a]pyridine scaffolds

Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances

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Direct Nucleophilic S_N1‐Type Reactions of Alcohols

Direct Nucleophilic S_N1‐Type Reactions of Alcohols