tetrakis(triphenylphosphine) palladium(0); sodium hydroxide in tetrahydrofuran; water 16 h; Inert atmosphereReflux;

1.1: 9-bora-bicyclo[3.3.1]nonane / toluene / 18 h / |Inert atmosphere; |Reflux 1.2: 2 h / 20 °C / |Inert atmosphere; |Reflux 2.1: sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) / water; tetrahydrofuran / 16 h / |Inert atmosphere; |Reflux View Scheme

1.1: toluene-4-sulfonic acid / benzene / |Inert atmosphere; |Reflux; |Dean-Stark 2.1: 9-bora-bicyclo[3.3.1]nonane / toluene / 18 h / |Inert atmosphere; |Reflux 2.2: 2 h / 20 °C / |Inert atmosphere; |Reflux 3.1: sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) / water; tetrahydrofuran / 16 h / |Inert atmosphere; |Reflux View Scheme

TPPTS; toluene-4-sulfonic acid; lithium chloride; 2-PyCOO-Pd-OTs in water; toluene T=115°C; Dehydration; Carbonylation; P=40504.1 Torr; 5 h; Title compound not separated from byproducts.;

TPPTS; toluene-4-sulfonic acid; lithium chloride; 2-PyCOO-Pd-OTs in water; toluene T=115°C; Dehydration; Carbonylation; P=40504.1 Torr; 5 h; Title compound not separated from byproducts.;

sodium hypochlorite; sodium chlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical in aq. phosphate buffer; water; acetonitrile T=20 - 35°C; pH=6.7; 6 h; Inert atmosphere;