Palladium(II) mediated aziridination of olefins with bromamine-T as the nitrogen source: scope and mechanism

Antunes, Alexandra M. M.; Bonifácio, Vasco D. B.; Nascimento, Susana; Lobo, Ana M.; Branco, Paula S.; Prabhakar, Sundaresan

doi:10.1016/j.tet.2007.05.020

Cited by 19 publications

(6 citation statements)

References 42 publications

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“…Olefins such as cinnamates, N , N -dimethylacrylamides, acrylonitrile, chalcone, etc could be transformed into the corresponding aziridines at room temperature in low yield. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity …”

Section: Aziridination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Aziridination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…Along with aziridination reactions via in-situ-generated phthalimidonitrene and ethoxycarbonylnitrene across olefins, palladium(II)-mediated aziridination of olefins with bromamine-T has been employed . Reaction of olefin 367 with bromamine-T in the presence of PdCl 2 or Pd(MeCN) 2 Cl 2 afforded the corresponding N -tosyl-2-(carboxymethyl)aziridine 368a in low yield (13–25%) (Scheme ).…”

Section: Synthesis Of 2-(carboxymethyl)aziridine Derivativesmentioning

confidence: 99%

Synthesis and Reactivity of 2-(Carboxymethyl)aziridine Derivatives

et al. 2014

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“…Pd II -promoted aziridination of olefins with bromamine-T to provide N -tosyl-2-substituted aziridines under mild conditions has been demonstrated by Branco (Scheme ) …”

Section: Organometallic Pdiv Compoundsmentioning

confidence: 99%

“…Pd II -promoted aziridination of olefins with bromamine-T to provide N-tosyl-2-substituted aziridines under mild conditions has been demonstrated by Branco (Scheme 244). 327 The study of reaction stereochemistry on deuterated olefins revealed interesting effects. Cis-deuteropropen-1-ol gave the cis-aziridine exclusively.…”

mentioning

confidence: 99%