Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)<sub>3</sub>‐Catalyzed Friedel–Crafts‐Type Benzylation

Yurino, Taiga; Hachiya, Asuka; Suzuki, Keisuke; Ohkuma, Takeshi

doi:10.1002/ejoc.202000077

Cited by 4 publications

References 85 publications

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Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

et al. 2021

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Eine Vielzahl funktionalisierter Triarylmethane und 1,1-Diarylalkanderivate wurdem ithilfe übergangsmetallfreier, Ein-Topf-oder Zwei-Schritt-Verfahren durch Reaktionen verschiedener Benzaldiacetate mit Organozinkreagenzien hergestellt. Eine sequentielle Kreuzkupplung ist durch einen Wechsel des Lçsungsmittels von THF auf Toluol mçglich. Ein zweitstufiger S N 1-artiger Mechanismus wurdev orgeschlagen und mittels experimenteller Studien bewiesen. Die Mçglichkeiten dieser Methodik wurde anhand der Synthese verschiedener biologischr elevanter Moleküle wie einem Anti-Tuberkulose-Wirkstoff,einem Anti-Brustkrebs-Wirkstoff,einer Vorstufe eines Sphingosin-1-phosphat (S1P)-Rezeptor-Modulators und eines FLAP-Inhibitors aufgezeigt.

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Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

et al. 2021

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Transition‐Metal‐Free Synthesis of Polyfunctional Triarylmethanes and 1,1‐Diarylalkanes by Sequential Cross‐Coupling of Benzal Diacetates with Organozinc Reagents

et al. 2021

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Avariety of functionalizedt riarylmethane and 1,1diarylalkane derivatives were prepared via at ransition-metalfree,one-pot and two-step procedure,involving the reaction of various benzal diacetates with organozinc reagents.Asequential cross-coupling is enabled by changing the solvent from THF to toluene,a nd at wo-step S N 1-type mechanism was proposed and evidenced by experimental studies.The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules,s uch as an anti-tuberculosis agent, an anti-breast cancer agent, ap recursor of as phingosine-1-phosphate (S1P) receptor modulator,a nd aFLAP inhibitor. Scheme 1. Typical methods for the synthesis of triarylmethanes and 1,1-diarylalkanes.

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Friedel-Crafts and related reactions catalyzed by solid acids

Török¹,

Schäfer²,

Kokel³

2022

Heterogeneous Catalysis in Sustainable Synthesis

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Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)₃‐Catalyzed Friedel–Crafts‐Type Benzylation

Abstract: Al(OTf ) 3 was identified as a high-performance catalyst for Friedel-Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 exam-Sapporo,

Cited by 4 publications

References 85 publications

Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

Transition‐Metal‐Free Synthesis of Polyfunctional Triarylmethanes and 1,1‐Diarylalkanes by Sequential Cross‐Coupling of Benzal Diacetates with Organozinc Reagents

Friedel-Crafts and related reactions catalyzed by solid acids

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Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3‐Catalyzed Friedel–Crafts‐Type Benzylation

Abstract: Al(OTf ) 3 was identified as a high-performance catalyst for Friedel-Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 exam-Sapporo,

Cited by 4 publications

References 85 publications

Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

Übergangsmetallfreie Synthese polyfunktioneller Triarylmethane und 1,1‐Diarylalkane durch sequentielle Kreuzkupplungen von Benzaldiacetaten mit Organozinkreagenzien

Transition‐Metal‐Free Synthesis of Polyfunctional Triarylmethanes and 1,1‐Diarylalkanes by Sequential Cross‐Coupling of Benzal Diacetates with Organozinc Reagents

Friedel-Crafts and related reactions catalyzed by solid acids

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Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)₃‐Catalyzed Friedel–Crafts‐Type Benzylation