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Research Article

Highly Regioselective Direct C-H Arylation: Facile Construction of Symmetrical Dithienophthalimide-Based π-Conjugated Molecules for Optoelectronics

Table 1

Conditions and yields for the direct C-H arylation with various brominated substituents.

EntryCompoundBr-Ar[Pd]aLigandaBaseaSolventaYield (%)

1DTI2MesBrMesPd(OAc)2PCy3K2CO3THFTrace
2DTI2MesBrMesPd(OAc)2PPh3K2CO3THF14
3DTI2MesBrMesPd(OAc)2P(o-Tol)3K2CO3THF19
4DTI2MesBrMesPd(OAc)2P(2-MeOPh)3K2CO3THF30
5DTI2MesBrMesPd(OAc)2P(2-MeOPh)3Cs2CO3THF33
6DTI2MesBrMesPd2(dba)3P(2-MeOPh)3Cs2CO3THF44
7DTI2MesBrMesPd2(dba)3P(2-MeOPh)3Cs2CO3DMF50
8DTI2MesBrMesPd2(dba)3P(2-MeOPh)3Cs2CO3Toluene63
9DTI2MesBrMesPd2(dba)3P(2-MeOPh)3Cs2CO3o-Xylene84
10DTI2CzBrCzPd2(dba)3P(2-MeOPh)3Cs2CO3o-XyleneTrace
11DTI2CzRBrCzRPd2(dba)3P(2-MeOPh)3Cs2CO3o-Xylene58
12DTI2TPABrTPAPd2(dba)3P(2-MeOPh)3Cs2CO3o-Xylene72
13DTI2FBrFPd2(dba)3P(2-MeOPh)3Cs2CO3o-Xylene61
14DTI2ThBrThPd2(dba)3P(2-MeOPh)3Cs2CO3o-XyleneTrace
15DTI2PyBrPyPd2(dba)3P(2-MeOPh)3Cs2CO3o-Xylene54
16DTI2PDIBrPDIPd2(dba)3P(2-MeOPh)3Cs2CO3o-XyleneTrace
17DTI2DPPBrDPPPd2(dba)3P(2-MeOPh)3Cs2CO3o-XyleneTrace
18DTI2NTIBrNTIPd2(dba)3P(2-MeOPh)3Cs2CO3o-Xylene63

aThe structures of ligands and palladium catalysts are shown in Figure S1. DTI (41.3 mg, 0.1 mmol, 1 equiv.), [Pd] (3 mol%), ligand (12 mol%), base (3.0 equiv.), pivalic acid (1 equiv.), and 0.1 M of THF in 85°C, DMF in 110°C, toluene in 100°C. and o-xylene in 120°C. Isolated yield was obtained from column chromatography.