Thiophene-3-boronic acid → 5,6-Dioctylnaphtho[2,1-b:3,4-b']dithiophene

HRID 713598

反応式

Br[C:2]1[S:6][C:5]2[C:7]3[S:8][C:9](Br)=[CH:10][C:11]=3[C:12]3[C:17]([C:4]=2[CH:3]=1)=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:13]=3.C([Mg]Br)CCCCCCC.C(C1C=CC=CC=1CCCCCCCC)CCCCCCC.S1C=CC(B(O)O)=C1>[Ni].[Pd].ClC1C=CC=CC=1Cl>[S:6]1[CH:2]=[CH:3][C:4]([C:17]2[C:12]([C:11]3[CH:10]=[CH:9][S:8][CH:7]=3)=[CH:13][C:14]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:16]=2)=[CH:5]1.[CH2:18]([C:15]1[CH:16]=[C:17]2[C:4]3[CH:3]=[CH:2][S:6][C:5]=3[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]2=[CH:13][C:14]=1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

参加物

実験手順

As outlined in Scheme 3, the preparation of 2,9-dibromo-5,6-dioctylnaphtho[2,1-b:3,4-b′]dithiophene started from 1,2-dichlorobenzene. A nickel-catalyzed Kumada coupling reaction between 1,2-dichlorobenzene and freshly prepared octylmagnesium bromide offered 1,2-dioctylbenzene. Iodination of 1,2-dioctylbenzene followed by palladium-catalyzed Suzuki coupling reaction with 3-thiophene boronic acid provided 4,5-bis(3-thienyl)-1,2-dioctylbenzene at high yield.18 5,6-dioctylnaphtho[2,1-b:3,4-b′]dithiophene was then prepared via oxidative photocyclization by irradiation of a diluted toluene solution of 4,5-bis(3-thienyl)-1,2-dioctylbenzene under ambient conditions in the presence of a catalytic amount of iodine.24,25 Subsequent bromination using NBS in a mixed solvent of chloroform/acetic acid offered the co-monomer 2,9-dibromo-5,6-dioctylnaphtho[2,1-b:3,4-b′]dithiophene

出典と根拠

ORDレコード: ord-c971ca9bb04a415ebd5c356aee531e7b
出典データセット: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09184390B2

反応式

参加物

反応物 4

生成物 2

試薬・触媒・溶媒 3

実験手順

出典と根拠

関連ノート