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Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction

Qian, Pengfei ; Zhang, Shilei ; Luo, Fan ; Wang, Jiarui ; Zhang, Xinyu ; Liu, Xuejun ; Chen, Xiaodong ; Wang, Wei ; Chen, Xiaobei

Chemical communications (Cambridge, England), 2022-10, Vol.58 (81), p.11458-11461 [Periódico revisado por pares]

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Título:
Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction
Autor: Qian, Pengfei ; Zhang, Shilei ; Luo, Fan ; Wang, Jiarui ; Zhang, Xinyu ; Liu, Xuejun ; Chen, Xiaodong ; Wang, Wei ; Chen, Xiaobei
Assuntos: Deuteration ; Deuterium ; Methane
É parte de: Chemical communications (Cambridge, England), 2022-10, Vol.58 (81), p.11458-11461
Notas: https://doi.org/10.1039/d2cc04959g
Electronic supplementary information (ESI) available. See DOI
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Descrição: An amine and bis(phenylsulfonyl)methane co-catalyzed hydrogen-deuterium exchange (HDE) method via a Michael-retro-Michael pathway for site-selective introduction of deuterium at the α-position of enals using D 2 O as a deuterium source has been achieved. The mild, operationally simple protocol allows for high yielding and high level deuterium incorporation (up to 99%) for structurally diverse aromatic-derived enals and dienals. An organocatalyzed reversible Michael reaction has been implemented for the α-position deuteration of enals with a high level of deuterium incorporation.
Editor: Cambridge: Royal Society of Chemistry
Idioma: Inglês

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