1-Bromo-2-nitrobenzene → 2-(2-Nitrophenyl)-2,3-dihydrofuran

HRID 1404522

反応式

HRID 1404522 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[CH:15]=[CH:14][CH2:13][CH2:12]1.C1C2C=CC(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2)CCC2C=CC(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2)C1.C1OC2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=C(C3C4OCCOC=4C=CC=3P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC1.C1OC2C(C3C4OCOC=4C=CC=3P(C3C=CC=CC=3)C3C=CC=CC=3)=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2O1.C1(P(C2C=CC=CC=2)C(CC(P(C2C=CC=CC=2)C2C=CC=CC=2)C)C)C=CC=CC=1>[Pd]>[O:11]1[CH:12]=[CH:13][CH2:14][CH:15]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

参加物

8

反応物 6

HCID 113411-Bromo-2-nitrobenzeneHCID 709342,3-DihydrofuranHCID 41858942,4-Bis(diphenylphosphino)pentaneHCID 10864772(R)-PhanephosHCID 110175104,4'-Bi-1,3-benzodioxole-5,5'-diylbis(diphenylphosphine)HCID 11193918Synphos

生成物 1

HCID 681084132-(2-Nitrophenyl)-2,3-dihydrofuran

試薬・触媒・溶媒 1

HCID 23938Palladium触媒4 回

実験手順

In certain embodiments, the palladium catalyst used in the Heck arylation reaction may be any suitable chiral palladium catalyst known to those skilled in the art. Examples of chiral palladium catalysts suitable for the Heck arylation reaction between bromonitrobenzene (IX) and 2,3-dihydrofuran include Pd(II) and Pd(0) complexes of 2,2′-bis(diphenylphosphino)binaphyl (BINAP), other BINAP-type ligands, JosiPhos, other JosiPhos-type ligands, PhanePhos, SynPhos, DifluoroPhos, SegPhos, P-Phos, TunePhos, 2,4-bis(diphenylphosphino)pentane, and PHox. Heck arylation reactions conducted using chiral palladium catalysts may afford enantiomerically-enriched dihydrofuranyl nitrobenzene(s) (VIIIa) and/or (VIIIb), wherein R is H or F. In some embodiments, the enantiomeric excess of dihydrofuranyl nitrobenzene(s) (VIIIa) and/or (VIIIb) may be between about 5-100%, about 10-100%, about 20-100%, about 30-100%, about 40-100%, about 50-100%, about 60-100%, about 70-100%, about 80-100%, about 85-100%, about 90-100%, about 91-100%, about 92-100%, about 93-100%, about 94-100%, about 95-100%, about 96-100%, about 97-100%, about 98-100%, about 99-100%, or about 100%. Thus, any chiral compound derived from the enantiomerically-enriched compound(s) of formula (VIIIa) and/or (VIIIb) may also contain an excess of one of the two enantiomers of the compound.

出典と根拠

ORDレコード
ord-f3d129944c624de9b0f51c718a56c7d6
出典データセット
uspto-grants-2014_12
特許番号
US08912326B2

関連ノート

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