High-Speed, Highly Fluorous Organic Reactions

Olofsson, Kristofer; Kim, Sun‐Young; Larhed, Mats; Curran, Dennis P.; Hallberg, Anders

doi:10.1021/jo982511y

Cited by 105 publications

(45 citation statements)

References 26 publications

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“…[197] Wetter and Studer have described radical carboaminoxylations of various nonactivated olefins and difficult radical cyclizations (Scheme 40). [198] Scheme 37.…”

Section: Radical Reactionsmentioning

confidence: 99%

“…[238] This was later followed by examples of radical reactions initiated by fluorous tin hydrides. [197] More recently there have been reports on very efficient Pd-catalyzed cross-coupling reactions of perfluoroalkylsulfonates with thiols, [239] and on the use of fluorous-tagged bidentate ligands in microwaveassisted Heck reactions of vinyl triflates with enamides (Scheme 50). [240] F-SPE was used to remove excess reagents or ligands, respectively, in the two cases.…”

Section: Reactions In Fluorous Phasesmentioning

confidence: 99%

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Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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“…[197] Wetter and Studer have described radical carboaminoxylations of various nonactivated olefins and difficult radical cyclizations (Scheme 40). [198] Scheme 37.…”

Section: Radical Reactionsmentioning

confidence: 99%

Section: Reactions In Fluorous Phasesmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…Upon cooling to 0 C, 1 was recovered in 92% yield. In the same year, Curran, Hallberg and co-workers reported, as part of a larger study, an isolated example in which the stannane 2 (Scheme 2.2) was similarly recovered [34]. This involved the reductive addition of adamantyl bromide to acrylonitrile, with in situ reduction of the resulting stannyl bromide by NaBH 3 CN.…”

Section: Two Early Examplesmentioning

confidence: 95%

Catalysis Involving Fluorous Phases: Fundamentals and Directions for Greener Methodologies

Gladysz

2010

Handbook of Green Chemistry

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This article briefly reviews the fundamentals of fluorous chemistry, with an emphasis on aspects most relevant to catalysis. The development of “greener” fluorous solvents and ponytails (phase tags) is described. Protocols that minimize the use of fluorous solvents are emphasized. Some of these exploit the highly temperature dependent solubilites of fluorous compounds in organic solvents, which can be fine‐tuned by varying the length and number of the (CF 2 ) n segments in the ponytails. Suitably designed fluorous catalysts can thus be employed under homogeneous conditions at elevated temperatures, and recovered by solid/liquid phase separation at lower temperatures. Fluorous solid supports such as fluoropolymers and fluorous silica gel can be used to aid the recovery of small catalyst quantities, and render phase separation more efficient. The use of CO 2 pressure as a non‐thermal solubility trigger, and catalyst recovery by solid phase extraction using non‐fluorous solvents, are also detailed.

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“…The product isolated from the fluorous layer was further purified by flash chromatography. To improve the efficiency of fluorous liquid-liquid extraction, a tin reagent with heavier fluorous tags (C 10 F 21 CH 2 CH 2 ) 3 has been developed for the Stille reactions [30].…”

Section: Fluorousmentioning

confidence: 99%

“…The Curran and Hallberg groups developed a heavy fluorous tin hydride 9 and used it under continuous microwave heating conditions for halide reduction and cyclization reactions (Scheme 12). Reactions were conducted in benzotrifluoride (BTF) to increase the solubility of the tin reagent [30]. Reaction mixtures were worked up by a three-phase extraction with FC-84, dichloromethane, and water.…”

Section: Free Radical Reactionsmentioning

confidence: 99%

Microwave-Enhanced High-Speed Fluorous Synthesis

Zhang

Microwave Methods in Organic Synthesis

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Increasing reaction speed and simplifying product purification are two major ways to improve the efficiency of organic synthesis. A new technology for high-speed solution-phase synthesis has been developed by combination of microwave heating and fluorous purification. This review describes different techniques for microwave-enhanced fluorous synthesis and their applications in Pdcatalyzed cross-coupling reactions, free-radical reactions, multicomponent reactions, and compound library synthesis.

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High-Speed, Highly Fluorous Organic Reactions

Cited by 105 publications

References 26 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Catalysis Involving Fluorous Phases: Fundamentals and Directions for Greener Methodologies

Microwave-Enhanced High-Speed Fluorous Synthesis

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