Asset Details
Do you wish to reserve the book?
Practical synthesis of C1 deuterated aldehydes enabled by NHC catalysis
Hey, we have placed the reservation for you!
By the way, why not check out events that you can attend while you pick your title.
Oops! Something went wrong.
Looks like we were not able to place the reservation. Kindly try again later.
Are you sure you want to remove the book from the shelf?
Practical synthesis of C1 deuterated aldehydes enabled by NHC catalysis
Do you wish to request the book?
Practical synthesis of C1 deuterated aldehydes enabled by NHC catalysis
Please be aware that the book you have requested cannot be checked out. If you would like to checkout this book, you can reserve another copy
We have requested the book for you!
Your request is successful and it will be processed during the Library working hours. Please check the status of your request in My Requests.
Oops! Something went wrong.
Looks like we were not able to place your request. Kindly try again later.
Journal Article
Practical synthesis of C1 deuterated aldehydes enabled by NHC catalysis
2019
Overview
The recent surge in applications of deuterated pharmaceutical agents has created an urgent demand for synthetic methods that efficiently generate deuterated building blocks. Here, we show that N-heterocyclic carbenes promote a reversible hydrogen–deuterium exchange reaction with simple aldehydes, which leads to a practical approach to synthetically valuable C1 deuterated aldehydes. The reactivity of the well-established N-heterocyclic carbene-catalysed formation of Breslow intermediates from aldehydes is reengineered to overcome the overwhelmingly kinetically favourable benzoin condensation reaction and achieve the critical reversibility to drive the formation of desired deuterated products when an excess of D
2
O is employed. Notably, this operationally simple and cost-effective protocol serves as a general and truly practical approach to all types of 1-D-aldehydes including aryl, alkyl and alkenyl aldehydes, and enables chemoselective late-stage deuterium incorporation into complex, native therapeutic agents and natural products with uniformly high levels (>95%) of deuterium incorporation for a total of 104 tested substrates.
Deuterated molecules are important both as labelled probes and as targets in their own right. Here the authors report a very simple and general deuteration of aldehydes, by the use of an N-heterocyclic carbene catalyst in the presence of D
2
O.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
