2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene T=100°C; 30 h;

manganese(IV) oxide in dichloromethane 18 h;

1.1: tert-butyllithium / hexane; diethyl ether / 1 h / -100 °C 1.2: 83 percent / hexane; diethyl ether / 2 h / -100 - -60 °C 2.1: 98 percent / MnO2 / CH2Cl2 / 18 h View Scheme

1.1: tert-butyllithium / hexane; diethyl ether / 1 h / -100 °C 1.2: 83 percent / hexane; diethyl ether / 2 h / -100 - -60 °C 2.1: 98 percent / MnO2 / CH2Cl2 / 18 h View Scheme

Friedel-Crafts acylation;

sodium hydride 1.) DMSO, RT, 10 min, 2.) DMSO, RT; Yield given. Multistep reaction;

1.1: potassium acetate; 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane / 1,4-dioxane / 0.17 h / Microwave irradiation; Inert atmosphere; Sealed vial; Sonication 1.2: 17 h / 100 °C / Inert atmosphere 1.3: 0.5 h 2.1: dipotassium peroxodisulfate; silver nitrate / water; 2,3,4-trifluorotoluene / 1 h / 60 °C View Scheme