A palladium-catalyzed deuterated formylation of aryl sulfonium salts is prepared conveniently from readily available arenes, which enables the expedient synthesis of a series of structurally diverse C-1 deuterated aldehydes with 96%-99% deuterium incorporation. The easy to handle and cost-effective DCOONa provides a deuterium source, which can be introduced onto the formyl units with excellent selectivity under the palladium-catalytic redox neutral conditions. This catalytic route can accomplish the direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C (sp2)-H thianthrenation. Moreover, on the basis of this practical approach, several deuterated drugs and analogues could be prepared with excellent levels of deuterium incorporation.
Palladium-Catalyzed Synthesis of C-1 Deuterated Aldehydes from (Hetero) Arenes Mediated by C (sp2)-H Thianthrenation / Zhao B.; Wang Q.; Zhu T.; Feng B.; Ma M.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 24:30(2022), pp. 5608-5613. [10.1021/acs.orglett.2c02328]
Palladium-Catalyzed Synthesis of C-1 Deuterated Aldehydes from (Hetero) Arenes Mediated by C (sp2)-H Thianthrenation
Zhao B.
;Wang Q.;
2022
Abstract
A palladium-catalyzed deuterated formylation of aryl sulfonium salts is prepared conveniently from readily available arenes, which enables the expedient synthesis of a series of structurally diverse C-1 deuterated aldehydes with 96%-99% deuterium incorporation. The easy to handle and cost-effective DCOONa provides a deuterium source, which can be introduced onto the formyl units with excellent selectivity under the palladium-catalytic redox neutral conditions. This catalytic route can accomplish the direct late-stage C-H functionalization of bioactive molecules and natural product derivatives assisted by C (sp2)-H thianthrenation. Moreover, on the basis of this practical approach, several deuterated drugs and analogues could be prepared with excellent levels of deuterium incorporation.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.