Synthesis of Alkenylphosphonates through Palladium-Catalyzed Coupling of α-Diazo Phosphonates with Benzyl or Allyl Halides

Zhou, Yujing; Ye, Fei; Wang, Xi; Xu, Shuai; Zhang, Yan; Wang, Jianbo

doi:10.1021/acs.joc.5b00629

Cited by 43 publications

(27 citation statements)

References 57 publications

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“…Indeed, TFA-induced reaction of 20 with P(OEt) 3 led to vinyl phosphonate 36 in 30% isolated yield. To the best of our knowledge, this reaction represents the first metal-free synthesis of a tetrasubstituted alkenyl phosphonate …”

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confidence: 99%

One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides

et al. 2018

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A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl, and alkyl triazenes. The synthetic utility of vinyl triazenes is demonstrated by acid-induced C-N, C-O, C-F, C-P, and C-S bond-forming reactions.

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confidence: 99%

One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides

et al. 2018

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“…In addition to aryl halide electrophiles, phenol-derived aryl electrophiles − and activated aryl fluorides can also participate in this type of reaction. In addition to the simple N -tosylhydrazones, the coupling of functionalized N -tosylhydrazones with aryl electrophiles can produce a wide range of functionalized olefins. − …”

Section: Ketones As Alkenyl Coupling Partnersmentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via N-Tosylhydrazones

2020

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Ketones and aldehydes play central roles in organic synthesis. There are numerous broadly used reactions that are related to the carbonyl reactivity, such as Grignard reactions, Wittig reactions, aldol reactions, and so on. In addition, the formation of enol triflates is a classic protocol that enables the ketones to be applied in transition-metal-catalyzed cross-coupling reactions, in which case the ketones are considered as the precursors of alkenyl electrophiles in the C−C bond-forming transformations. In the past decade, a new type of ketone-or aldehyde-based C−C bond-forming transformations has emerged. In this type of reactions, the ketones or aldehydes are first converted to their corresponding N-tosylhydrazones, which are employed as reaction partners in various transition-metal-catalyzed carbene-based cross-coupling reactions. The N-tosylhydrazone-based carbene couplings significantly enhance the potential of ketones and aldehydes in modern organic synthesis. This Perspective aims to give an overview of carbene coupling reactions with N-tosylhydrazones from the viewpoint of exploring new potentials of ketones and aldehydes in organic synthesis.

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“…In addition, methods involving metal‐catalyzed olefin methasis or Heck‐type crossing coupling of vinylphosphonates with aryl halides or aryldiazonium salts were also established. Very recently, a new strategy was reported on the synthesis of trisubstituted alkenylphosphonates via palladium‐catalyzed cross‐coupling of α‐diazo phosphonates with allyl or benzyl halides . Alkenes direct phosphonylation should be an ideal and complimentary strategy towards the synthesis of alkenylphosphonate derivatives.…”

Section: Introductionmentioning

confidence: 99%

TEMPO and Silver‐Mediated Intermolecular Phosphonylation of Alkenes: Stereoselective Synthesis of (E)‐Alkenylphosphonates

et al. 2019

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An efficient method was developed towards the synthesis of alkenylphosphonates from simple olefins and phosphonate diesters. This method was enabled by the use of cheap and commercially available silver salts and TEMPO. This method exhibits of good functional group tolerance, specific (E)‐selectivity for all olefins and vinyl selectivity for aliphatic olefins. A radical mechanism was proposed, and TEMPO was involved in the product formation step.

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Synthesis of Alkenylphosphonates through Palladium-Catalyzed Coupling of α-Diazo Phosphonates with Benzyl or Allyl Halides

Cited by 43 publications

References 57 publications

One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides

One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides

Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via N-Tosylhydrazones

TEMPO and Silver‐Mediated Intermolecular Phosphonylation of Alkenes: Stereoselective Synthesis of (E)‐Alkenylphosphonates

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