1: With n-butyllithium in tetrahydrofuran T=-78°C; 2: With boric acid trimethyl ester 3: With methanol Further stages.;

1: 3-bromo-1-(triisopropylsilyl)pyrrole With n-butyllithium in tetrahydrofuran T=-78°C; 0.5 h; Inert atmosphere; 2: boric acid trimethyl ester in tetrahydrofuran T=-78 - 20°C; 1 h; 3: With water in tetrahydrofuran

1: 3-iodo-1-(triisopropylsilyl)-1H-pyrrole With tert.-butyl lithium in tetrahydrofuran T=-78°C; 2: boric acid trimethyl ester 3: Heating;

1.1: 88 percent / NBS / tetrahydrofuran / -78 °C 2.1: n-BuLi / tetrahydrofuran / -78 °C 2.2: B(OCH3)3 2.3: 50 percent / aq. MeOH View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 - 20 °C / Inert atmosphere 1.2: 0.5 h / -78 - 20 °C 2.1: N-bromosuccinmide / tetrahydrofuran / 3 h / -78 - 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 - 20 °C View Scheme

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in methanol; benzene 16 h; Heating;