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Sodium Carbonate → 5-Trimethylsilylethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene

HRID 426430
Notes
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Reaction equation

HRID 426430 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[CH3:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]1[S:18][CH:19]=[CH:20][C:21]=1[C:22]1[C:23]2[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=2[S:25][C:26]=1[CH3:27].[CH3:32][C:33]1SC2C=CC=CC=2C=1B(O)O.BrC1SC=CC=1Br.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>[Pd].ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.O>[CH3:1][Si:2]([C:5]#[C:6][C:19]1[S:18][C:17]([C:9]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:8]=2[CH3:7])=[C:21]([C:22]2[C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[S:25][C:26]=2[CH3:27])[CH:20]=1)([CH3:4])[CH3:3].[C:32]([C:20]1[C:21]([C:22]2[C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[S:25][C:26]=2[CH3:27])=[C:17]([C:9]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:8]=2[CH3:7])[S:18][CH:19]=1)#[CH:33]
ParticipantsProcedureSources & evidenceReaction notes

Participants

13

Reactant 6

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 66111TrimethylsilylacetyleneHCID 765902,3-DibromothiopheneHCID 58933004(2-Methyl-1-benzothiophen-3-yl)boronic acidHCID 667041632,3-Bis(2-methylbenzothiophen-3-yl)thiophene

Product 2

HCID 66704311
5-Trimethylsilylethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene
HCID 87118226Ethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Trimethylsilylethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene is synthesized by the Sonogashira coupling reaction of trimethylsilylacetylene and the bromo-derivative of 2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene, which is also prepared from the Suzuki cross-coupling reaction of 2.5 equivalents of 2-methyl-3-benzo[3,2-b]thienylboronic acid and 2,3-dibromothiophene in the presence of the palladium catalyst, Pd(PPh3)4, and sodium carbonate in a heterogeneous mixture of water and THF according to the procedure similar to that of (L1). Subsequent deprotection of the trimethylsilyl group using potassium carbonate in dichloromethane solution gives the target ligand ethynyl-2,3-bis-(2-methyl-3-benzo[3,2-b]thienyl)thiophene (L5). The synthetic route is shown in FIG. 12. Excitation of the ligand with λ≦352 nm light resulted in the formation of the close form, corresponding to the photocyclization product.

Sources & evidence

ORD record
ord-a5694d3d684a47aaa9adec4d64fca1ec
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08107150B2

Reaction notes

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