2017
DOI: 10.1002/anie.201707719
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Copper‐Catalyzed C(sp3)−H/C(sp3)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

Abstract: The first oxidative C(sp )-H/C(sp )-H cross-dehydrogenative coupling (CDC) reaction promoted by an internal oxidant is reported. This copper-catalyzed CDC reaction of oxime acetates and trifluoromethyl ketones provides a simple and efficient approach towards 2-trifluoromethyldihydropyrrol-2-ol derivatives in a highly diastereoselective manner by cascade C(sp )-C(sp ) bond formation and cyclization. These products were further transformed into various significant and useful trifluoromethylated heterocyclic comp… Show more

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Cited by 79 publications
(25 citation statements)
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“…Furthermore, enones with aromatic rings such as 2‐naphthyl group and 3‐furyl group afforded the desired product 3l and 3m in 63 % and 56 % yields, respectively. Reaction of chalcone 1n gave a desired product 3n in 89 % yield.…”
Section: Resultsmentioning
confidence: 99%
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“…Furthermore, enones with aromatic rings such as 2‐naphthyl group and 3‐furyl group afforded the desired product 3l and 3m in 63 % and 56 % yields, respectively. Reaction of chalcone 1n gave a desired product 3n in 89 % yield.…”
Section: Resultsmentioning
confidence: 99%
“…5,5,5‐Trifluoro‐1,3‐diphenylpentane‐1,4‐dione (3n): 89 % total yield (273 mg), pale yellow solid. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 3.47 (1H, dd, J = 3.4 Hz, J = 18.2 Hz), 4.08 (1H, dd, J = 11.0 Hz, J = 18.2 Hz), 4.78 (1H, dd, J = 3.4 Hz, J = 11.0 Hz), 7.31–7.48 (7H, m), 7.59 (1H, t, J = 7.3 Hz), 7.95–7.97 (2H, m).…”
Section: Methodsmentioning
confidence: 99%
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“…Furthermore, the formyl group could selectively undergo olefination with ethyl‐2‐(diethoxyphosphoryl)acetate to give the highly unsaturated ethyl‐( E )‐4‐(2‐oxo‐2‐phenylethyl)‐6,6‐diphenylhexa‐2,5‐dienoate ( 6 ) in 85 % yield (Scheme c) . Highly substituted pyrrole derivatives could be obtained through Paal–Knorr reactions (Scheme d) . Notably, large conjugated bipyrrole 8 could be constructed when a diamine was reacted with 3 na (Scheme e); such pyrrole‐derived compounds are sought‐after fragments in material science .…”
Section: Figurementioning
confidence: 99%
“…This internal oxidant system tolerate diverse valuable functional groups on the aryl ring of the oxime acetate,such as alkoxy,methylthio, morpholinyl, amino,halo,cyano,ester, trifluoromethyl, nitro, and sulfonyl groups (products 3g-3z), providing ample potential for further synthetic applications.S ignificantly, product 3a was crystalline,a nd its structure and relative stereochemistry were thus determined by X-ray crystallographic analysis. [10] Oxime acetates derived from 1-(naphthalen-2-yl)ethan-1-one and 1-(benzo [d] [1,3]dioxol-5-yl)ethan-1-one delivered the desired products in high yields (3aa and 3ab). Furthermore,d ifferent heteroaromatic groups,s uch as furanyl, thienyl, pyrrolyl, and pyridyl, were also tolerated on the oxime,a nd the corresponding products 3ac-3aj were obtained in acceptable yields.H owever,t he desired product (3ak)w as not observed when oxime acetate 2ak,w hich is derived from an aliphatic ketone,w as used as the substrate.…”
mentioning
confidence: 99%