Graduate School of Sciences and Technology for Innovation and ‡Department of Biology and Chemistry, Yamaguchi University , Yamaguchi 753-8512, Japan.
Org Lett. 2016 Oct 7;18(19):4912-4915. doi: 10.1021/acs.orglett.6b02391. Epub 2016 Sep 26.
Photoinduced catalytic Michael-type radical addition was achieved via olefin insertion into a nonacidic C(sp)-H bond, utilizing 2-chloroanthraquinone as a C-H bond-cleaving catalyst and 1,1-bis(phenylsulfonyl)ethylene as an olefinic substrate. The present radical protocol allows carbon chain extension stemming from nonacidic C-H bonds, which complements alkylation at acidic C-H bonds under ionic conditions and installs the active methine site that acts as a versatile synthetic handle for further transformations.
通过烯烃插入非酸性 C(sp)-H 键，利用 2-氯蒽醌作为 C-H 键断裂催化剂和 1,1-双(苯磺酰基)乙烯作为烯烃底物，实现了光诱导催化的迈克尔型自由基加成。本自由基方案允许源自非酸性 C-H 键的碳链延伸，这补充了离子条件下酸性 C-H 键的烷基化，并安装了作为进一步转化的多功能合成手柄的活性亚甲基金属位点。
