Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 64221Generated: October 29, 2026

Toluene → 2-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene

https://huagongshe.com/reaction/64221

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant2-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 68015595—
Reactant2-(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene Benzo[b]benzo[4,5]thieno[3,2-d]thiophen-2-yl trifluoromethanesulfonateHCID 118130601—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Catalyst2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
SolventWaterHCID 962—
Product2-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiopheneHCID 8668940978%

Reaction Steps

Synthesis of 2-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene Benzo[b]benzo[4,5]thieno[3,2-d]thiophen-2-yl trifluoromethanesulfonate (1.3 g, 3.35 mmol), Pd2(dba)3 (0.061 g, 0.067 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.11 g, 0.268 mmol), 2-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.625 g, 3.51 mmol), K3PO4 (2.13 g, 10.04 mmol), toluene (90 mL) and water (10 mL) were charged in a 250 mL flask. This mixture was bubbled with nitrogen for 30 minutes then heated to reflux overnight. After purification, 1.5 g (78%) of a white solid was obtained. The compound was confirmed by NMR.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09447113B2
Source datasetuspto-grants-2016_09
ORD IDord-3dc8ec0aedd749c6b26b7ec33a7d586b
Source noteuspto-grants-2016_09