Jang Jin Hyeok, Ahn Seongmo, Park Soo Eun, Kim Soeun, Byon Hye Ryung, Joo Jung Min
Department of Chemistry and Chemistry Institute for Functional Materials , Pusan National University , Busan 46241 , Republic of Korea.
Department of Chemistry at Korea Advanced Institute of Science and Technology (KAIST) and Advanced Battery Center at KAIST Institute for NanoCentury , 291 Daehak-ro , Yuseong-gu, Daejeon 34141 , Republic of Korea.
Org Lett. 2020 Feb 21;22(4):1280-1285. doi: 10.1021/acs.orglett.9b04545. Epub 2020 Feb 6.
Pd-catalyzed C-H annulation reactions of halo- and aryl-heteroarenes were developed using readily available -bromobiaryls and -dibromoaryls, respectively. A variety of five-membered heteroarenes rapidly provided the corresponding phenanthrene-fused heteroarenes, which led to the identification of phenanthro-pyrazole and thiazole as new, stable -2 V redox couples. The flexible syntheses and tunability of the redox potentials of these azole-fused phenanthrenes over a wide range are expected to facilitate their application as redox-active organic functional materials.
分别使用易于获得的β-溴代联芳基和二溴代芳基，开发了钯催化的卤代杂芳烃和芳基杂芳烃的C-H环化反应。各种五元杂芳烃能迅速生成相应的菲稠合杂芳烃，这使得菲并吡唑和噻唑被鉴定为新的、稳定的-2V氧化还原对。这些唑稠合菲的灵活合成方法以及氧化还原电位在很宽范围内的可调性，有望促进它们作为氧化还原活性有机功能材料的应用。
