通过钯催化的迭代C(sp(2))-H键芳基化高效合成含氟亚苯基单元的π共轭分子。
Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp(2))-H bond arylations.
作者信息
Abdelmalek Fatiha, Derridj Fazia, Djebbar Safia, Soulé Jean-François, Doucet Henri
机构信息
Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France ; Département de Chimie, UMMTO, University, BP 17 RP, 15000 Tizi-Ouzou, Algeria.
Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 "Organométalliques, Matériaux et Catalyse", Campus de Beaulieu, 35042 Rennes, France ; Département de Chimie, UMMTO, University, BP 17 RP, 15000 Tizi-Ouzou, Algeria ; Laboratoire d'hydrométallurgie et chimie inorganique moléculaire, Faculté de Chimie, U.S.T.H.B. Bab-Ezzouar, Algeria.
出版信息
Beilstein J Org Chem. 2015 Oct 28;11:2012-20. doi: 10.3762/bjoc.11.218. eCollection 2015.
We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C-H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad heteroaromatic compounds via regioselective activation of C(sp(2))-H bonds.
我们在此报告通过迭代C-H键芳基化反应两步或三步合成氟化π共轭低聚物的方法。第一步，钯催化的杂芳烃脱硫芳基化反应能够高产率地合成氟芳基-杂芳烃单元。然后，接下来的步骤涉及由PdCl(C₃H₅)(dppb)催化的与芳基溴的直接芳基化反应，通过C(sp²)-H键的区域选择性活化得到三联或四联杂芳族化合物。
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