4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 81, Pages 11458-11461

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc04959g

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Funding

  1. National Natural Science Foundation of China [22071053, 22271206]
  2. Shanghai Frontiers Science Center of Optogenetic Techniques for CellMetabolism (Shanghai Municipal Education Commission) [2021 Sci Tech 03-28]
  3. PAPD (Priority Academic Program Development of Jiangsu Higher Education Institutions)

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A co-catalyzed hydrogen-deuterium exchange method has been developed to selectively introduce deuterium at a specific position of enals. The protocol is mild and simple, allowing for high level deuterium incorporation in structurally diverse aromatic-derived enals and dienals.
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 ccposition of enals using D2O 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.

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