New developments in gold-catalyzed manipulation of inactivated alkenes
- Michel Chiarucci and
- Marco Bandini
Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294
Graphical Abstract
Figure 1: Elementary steps in the gold-catalyzed nucleophilic addition to olefins.
Figure 2: Different approaches for the gold-catalyzed manipulation of inactivated alkenes.
Figure 3: Computed mechanistic cycle for the gold-catalyzed alkoxylation of ethylene with PhOH.
Scheme 1: [Au(I)]-catalyzed addition of phenols and carboxylic acids to alkenes.
Scheme 2: [Au(III)] catalyzed annulations of phenols and naphthols with dienes.
Scheme 3: [Au(III)]-catalyzed addition of aliphatic alcohols to alkenes.
Scheme 4: [Au(III)]-catalyzed carboalkoxylation of alkenes with dimethyl acetals 6.
Figure 4: Postulated mechanism for the [Au(I)]-catalyzed hydroamination of olefins.
Scheme 5: Isolation and reactivity of alkyl gold intermediates in the intramolecular hydroamination of alkene...
Scheme 6: [Au(I)]-catalyzed intermolecular hydroamination of dienes.
Scheme 7: Intramolecular [Au(I)]-catalyzed hydroamination of alkenes with carbamates.
Scheme 8: [Au(I)]-catalyzed inter- as well as intramolecular addition of sulfonamides to isolated alkenes.
Scheme 9: Intramolecular hydroamination of N-alkenylureas catalyzed by gold(I) carbene complex.
Scheme 10: Enantioselective hydroamination of alkenyl ureas with biphenyl tropos ligand and chiral silver phos...
Scheme 11: Intramolecular [Au(I)]-catalyzed hydroamination of N-allyl-N’-aryl ureas. (PNP = pNO2-C6H4, PMP = p...
Scheme 12: [Au(I)]-catalyzed hydroamination of alkenes with ammonium salts.
Scheme 13: Enantioselective [Au(I)]-catalyzed intermolecular hydroamination of alkenes with cyclic ureas.
Scheme 14: Mechanistic proposal for the cooperative [Au(I)]/menthol catalysis for the enantioselective intramo...
Scheme 15: [Au(III)]-catalyzed addition of 1,3-diketones to alkenes.
Scheme 16: [Au(I)]-catalyzed intramolecular addition of β-keto amides to alkenes.
Scheme 17: Intermolecular [Au(I)]-catalyzed addition of indoles to alkenes.
Scheme 18: Intermolecular [Au(III)]-catalyzed hydroarylation of alkenes with benzene derivatives and thiophene....
Scheme 19: a) Intramolecular [Au(III)]-catalyzed hydroarylation of alkenes. b) A SEAr-type mechanism was hypot...
Scheme 20: Intramolecular [Au(I)]-catalyzed hydroalkylation of alkenes with simple ketones.
Scheme 21: Proposed reaction mechanism for the intramolecular [Au(I)]-catalyzed hydroalkylation of alkenes wit...
Scheme 22: Tandem Michael addition/hydroalkylation catalyzed by [Au(I)] and [Ag(I)] salts.
Scheme 23: Intramolecular [Au(I)]-catalyzed tandem migration/[2 + 2] cycloaddition of 1,7-enyne benzoates.
Scheme 24: Intramolecular [Au(I)]-catalyzed cyclopropanation of alkenes.
Scheme 25: Stereospecificity in [Au(I)]-catalyzed hydroalkoxylation of allylic alcohols.
Scheme 26: Mechanistic investigation on the intramolecular [Au(I)]-catalyzed hydroalkoxylation of allylic alco...
Scheme 27: Mechanistic investigation on the intramolecular enantioselective [Au(I)]-catalyzed alkylation of in...
Scheme 28: Synthesis of (+)-isoaltholactone via stereospecific intramolecular [Au(I)]-catalyzed alkoxylation o...
Scheme 29: Intramolecular enantioselective dehydrative amination of allylic alcohols catalyzed by chiral [Au(I...
Scheme 30: Enantioselective intramolecular hydroalkylation of allylic alcohols with aldehydes catalyzed by 20c...
Scheme 31: Gold-catalyzed intramolecular diamination of alkenes.
Scheme 32: Gold-catalyzed aminooxygenation and aminoarylation of alkenes.
Scheme 33: Gold-catalyzed carboamination, carboalkoxylation and carbolactonization of terminal alkenes with ar...
Scheme 34: Synthesis of tricyclic indolines via gold-catalyzed formal [3 + 2] cycloaddition.
Scheme 35: Gold(I) catalyzed aminoarylation of terminal alkenes in presence of Selectfluor [dppm = bis(dipheny...
Scheme 36: Mechanistic investigation on the aminoarylation of terminal alkenes by bimetallic gold(I) catalysis...
Scheme 37: Proposed mechanism for the aminoarylation of alkenes via [Au(I)-Au(I)]/[Au(II)-Au(II)] redox cataly...
Scheme 38: Oxyarylation of terminal olefins via redox gold catalysis.
Scheme 39: a) Intramolecular gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes. b) Oxyaryl...
Scheme 40: Oxy- and amino-arylation of alkenes by [Au(I)]/[Au(III)] photoredox catalysis.
Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols
- Michel Chiarucci,
- Mirko Locritani,
- Gianpiero Cera and
- Marco Bandini
Beilstein J. Org. Chem. 2011, 7, 1198–1204, doi:10.3762/bjoc.7.139
Graphical Abstract
Figure 1: Working hypothesis for the present gold-catalyzed oxaallylic alkylation reaction.
Scheme 1: Gold-catalyzed synthesis of γ-lactones 4 from the corresponding monoesters 3.
Scheme 2: Mechanistic sketch of the gold-promoted oxaallylic alkylation reaction.
