Multi-step reaction with 13 steps
1.1: n-butyllithium; lithium diisopropyl amide; borane-ammonia complex / hexane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
2.2: 0.75 h / -78 - 0 °C / Inert atmosphere
3.1: triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
3.2: 2.75 h / 0 - 20 °C / Inert atmosphere
4.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C / Inert atmosphere
4.2: 18 h / -78 - 20 °C / Inert atmosphere
5.1: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
5.2: 0.17 h / -78 °C / Inert atmosphere
6.1: trimethylamine-N-oxide; potassium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water / 1.5 h / 70 °C / Inert atmosphere
7.1: copper(l) cyanide / tetrahydrofuran / 0.67 h / -50 - -10 °C / Inert atmosphere
7.2: 0.5 h / -50 - -10 °C / Inert atmosphere
7.3: 2 h / -50 - -10 °C / Inert atmosphere
8.1: Dess-Martin periodane / dichloromethane / 1.5 h / Inert atmosphere
9.1: sodium dihydrogenphosphate; dihydrogen peroxide / water; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere
9.2: 16 h / 0 °C / Inert atmosphere
10.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 2.25 h / 0 - 20 °C / Inert atmosphere
11.1: N-iodo-succinimide; 2,6-dimethylpyridine / 0.03 h / 0 °C / Inert atmosphere
12.1: dichloro bis(acetonitrile) palladium(II); triphenyl-arsane; Tetrabutylammoniumsalz der Diphenylphosphinsaeure / N,N-dimethyl-formamide / 20 h / 20 °C / Darkness; Inert atmosphere; Schlenk technique
12.2: 0.08 h / Inert atmosphere; Darkness; Schlenk technique
12.3: 18 h / Inert atmosphere; Schlenk technique; Darkness
13.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 16 h / 20 °C / Darkness; Inert atmosphere
With
2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium dihydrogenphosphate; N-iodo-succinimide; n-butyllithium; borane-ammonia complex; oxalyl dichloride; trimethylamine-N-oxide; triphenyl-arsane; tris(dimethylamino)sulfonium trimethylsilyldifluoride; dihydrogen peroxide; copper(l) cyanide; Dess-Martin periodane; dimethyl sulfoxide; triphenylphosphine; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; potassium hydroxide; lithium diisopropyl amide; diethylazodicarboxylate;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
3.1: |Corey-Fuchs Alkyne Synthesis / 4.1: |Corey-Fuchs Alkyne Synthesis / 4.2: |Corey-Fuchs Alkyne Synthesis;
DOI:10.1002/anie.201702189