Iodobenzene → 2,2'-Bis(diphenylamino)-9,9'-spirobifluorene

Participants

Role	Name	HCID	Charge
Reactant	Iodobenzene	HCID 11575	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	9,9'-Spirobi[fluorene]-2,2'-diamine	HCID 15415866	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene	HCID 1140	—
Product	2,2'-Bis(diphenylamino)-9,9'-spirobifluorene	HCID 20733885	—

Reaction Steps

2,2′-diamino-9,9′-spirobifluorene (3.46 g, 10 mmol), iodobenzene (6.8 mL, 60 mmol), Pd(OAc)2 (0.112 g, 0.5 mmol), sodium-tert-butoxide (14.4 g, 150 mmol) and tri-tert-butylphosphine (20 mL, 0.05 M in toluene, 1.0 mmol) were mixed in a flask containing with toluene (100 mL). The mixture was refluxed overnight. The solution was quenched with water and extracted twice with chloroform. The combined organic extracts were dried over MgSO4 and concentrated by rotary evaporation. Column chromatography on silica gel (hexane/chloroform=4/1) afforded products [2,2′-Bis(diphenylamino)-9,9′-spirobifluorene, hereinafter named as 22DPSF] as a white solid (4.5 g, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07714145B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-3e81e2c92edb4ea69c3c5b1fa0ea0688
Source note	uspto-grants-2010_05