Ortho-Deuteration of Aromatic Aldehydes via a Transient Directing Group-Enabled Pd-Catalyzed Hydrogen Isotope Exchange,The Journal of Organic Chemistry

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Ortho-Deuteration of Aromatic Aldehydes via a Transient Directing Group-Enabled Pd-Catalyzed Hydrogen Isotope Exchange
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-09-13 , DOI: 10.1021/acs.joc.1c01411
Junhua Kong _{1,

2} , Zhi-Jiang Jiang ₁ , Jiayuan Xu ₃ , Yan Li _{1,

2} , Hong Cao ₁ , Yanan Ding ₁ , Bencan Tang ₃ , Jia Chen ₁ , Zhanghua Gao ₁

Affiliation

A practical and scalable ortho-selective deuteration of aromatic aldehydes was accomplished by Pd-catalyzed hydrogen isotope exchange with deuterium oxide as an inexpensive deuterium source. The use of tert-leucine as a transient directing group facilitates the exchange, affording a wide range of ortho-deuterated aromatic aldehydes with deuterium incorporation up to 97%. The control experiments suggest that the addition of silver trifluoroacetate resists the unexpected reduction of Pd(II), while the theoretical study indicates a rapid reversible concerted metalation–deprotonation process.

中文翻译：

通过瞬态导向基团启用的 Pd 催化氢同位素交换对芳香醛进行邻位氘化

通过与作为廉价氘源的氧化氘进行 Pd 催化的氢同位素交换，实现了芳香醛的实用且可扩展的邻位选择性氘化。使用叔亮氨酸作为瞬态导向基团促进了交换，提供了多种氘掺入率高达 97% 的邻位氘代芳香醛。对照实验表明，三氟乙酸银的加入可以抵抗 Pd(II) 的意外还原，而理论研究表明，这是一个快速可逆的协同金属化-去质子化过程。

更新日期：2021-10-01

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