2019
DOI: 10.1039/c9ob01602c
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Application of copper(i) salt and fluoride promoted Stille coupling reactions in the synthesis of bioactive molecules

Abstract: This review summarises the synthesis of bioactive molecules through the use of Cu(i) salt and fluoride promoted Stille coupling reactions.

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Cited by 35 publications
(21 citation statements)
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“…On the first step, the crude reaction mixture obtained was added to an aqueous solution of potassium fluoride (KF) according to a reported literature procedure using an alcoholic KF solution [51]. The KF solution was allowed to react with the tin by-product in the mixture, so that the tin by-product precipitates into a white powder of polymeric Bu 3 SnF [2] and is removed by filtration. This was repeated until no residue was observed in the flask.…”
Section: Purification Of Crude Product Mixture From Pd-catalyzed Stilmentioning
confidence: 99%
See 1 more Smart Citation
“…On the first step, the crude reaction mixture obtained was added to an aqueous solution of potassium fluoride (KF) according to a reported literature procedure using an alcoholic KF solution [51]. The KF solution was allowed to react with the tin by-product in the mixture, so that the tin by-product precipitates into a white powder of polymeric Bu 3 SnF [2] and is removed by filtration. This was repeated until no residue was observed in the flask.…”
Section: Purification Of Crude Product Mixture From Pd-catalyzed Stilmentioning
confidence: 99%
“…Most importantly, the Stille, Suzuki-Miyaura, Heck, Negishi and Sonogashira coupling reactions typically catalyzed by palladium have been abundantly used in syntheses and widely studied in recent decades. Stille coupling, which is the palladium-catalyzed cross-coupling of an organostannane and an organohalide, is one of the most powerful methods for the straightforward joining together of carbon-carbon bonds in synthetic chemistry [1][2][3]. It is currently a widely used cross-coupling method for the synthesis of functional molecules and polymers, both in laboratory research and in industry [1,4].…”
Section: Introductionmentioning
confidence: 99%
“…Copper iodide (CuI) has a wide application in nonlinear optics [1,2], solar cells development [3], photocatalysis [4], photoluminescention [5], electrophysics [6,7] and conventional analytical chemistry, i.e., mercury detection [8]. Apart from those, CuI is used as a perspective catalyst in a large number of organic synthesis, viz., Heck-types reactions [9,10], Stills-types [11], Ullmann-type routes [12][13][14][15][16][17][18][19] Suzuki-Miyaura and Sonogashira reactions of cross-coupling [20][21][22] and many others [19,[22][23][24][25][26][27]. In addition, CuI was reported as an effective electrocatalyst in hydrazine-related synthesis [28] and formic acid oxidation [29].…”
Section: Introductionmentioning
confidence: 99%
“…An earlier report on the total synthesis of oxazolomycins provides an overview of the author's synthetic efforts toward neooxazolomycin (4), oxazolomycin A (5a), and related antibiotics [17]. The recent review of Lee has mainly focused on the application of copper(I) salt and fluoridepromoted Stille coupling reactions in the synthesis of bioactive molecules including inthomycins A-C (1-3) [18]. The present review provides a systematic summary of synthetic strategies for the synthesis of inthomycins and their analogues over the period of 1999 to present.…”
Section: Introductionmentioning
confidence: 99%