Division of Chemical Sciences, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.
Department of Chemistry, University of California , Berkeley, California 94720, United States.
J Am Chem Soc. 2015 Sep 30;137(38):12215-8. doi: 10.1021/jacs.5b08039. Epub 2015 Sep 16.
We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)2 and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to α-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.
我们报告了杂芳环（包括吡咯、吲哚、苯并呋喃和呋喃）C2 位 C-H 键与未活化的末端和内部烯烃的催化加成。该反应由 Ni(COD)2 和空间位阻大、富电子的 N-杂环卡宾配体或其类似的 Ni(NHC)(芳基)配合物共同催化。该反应对α-烯烃的反马氏加成具有高度选择性，同时也可以从内部烯烃生成线性烷基杂芳烃。该反应适用于含有酮、酯、酰胺、硼酸酯、硅醚、砜酰胺、缩醛、和游离胺的底物。
