通过需氧氧化Heck反应实现磷香豆素的烯基化及其在荧光苯并磷香豆素合成中的应用

Alkenylation of phosphacoumarins via aerobic oxidative Heck reactions and their synthetic application to fluorescent benzophosphacoumarins.

作者信息

Kim Cheol-Eui, Son Jeong-Yu, Shin Seohyun, Seo Boram, Lee Phil Ho

机构信息

National Creative Research Initiative Center for Catalytic Organic Reactions, Department of Chemistry, Kangwon National University , Chuncheon 200-701, Republic of Korea.

出版信息

Org Lett. 2015 Feb 20;17(4):908-11. doi: 10.1021/acs.orglett.5b00020. Epub 2015 Feb 3.

DOI:10.1021/acs.orglett.5b00020

PMID:25644690

Abstract

Alkenylation of phosphacoumarins is developed from the reaction of phosphacoumarins with a variety of activated as well as nonactivated alkenes via aerobic oxidative Heck reactions. In addition, 3-alkenylphosphacoumarins undergo an inverse electron demand Diels-Alder reaction (IEDDA) with enamines in situ generated from ketone and pyrrolidine followed by 1,2-elimination and a dehydrogenation, producing fluorescent benzophosphacoumarins.

摘要

通过有氧氧化Heck反应，磷香豆素与各种活化和未活化的烯烃反应，实现了磷香豆素的烯基化。此外，3-烯基磷香豆素与由酮和吡咯烷原位生成的烯胺发生逆电子需求Diels-Alder反应（IEDDA），随后进行1,2-消除和脱氢反应，生成荧光苯并磷香豆素。