The arene–alkene photocycloaddition
- Ursula Streit and
- Christian G. Bochet
Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61
Graphical Abstract
Scheme 1: Photochemistry of benzene.
Scheme 2: Three distinct modes of photocycloaddition of arenes to alkenes.
Scheme 3: Mode selectivity with respect of the free enthalpy of the radical ion pair formation.
Scheme 4: Photocycloaddition shows lack of mode selectivity.
Scheme 5: Mechanism of the meta photocycloaddition.
Scheme 6: Evidence of biradiacal involved in meta photocycloaddition by Reedich and Sheridan.
Scheme 7: Regioselectivity with electron withdrawing and electron donating substituents.
Scheme 8: Closure of cyclopropyl ring affords regioisomers.
Scheme 9: Endo versus exo product in the photocycloaddition of pentene to anisole [33].
Scheme 10: Regio- and stereoselectivity in the photocycloaddition of cyclopentene with a protected isoindoline....
Scheme 11: 2,6- and 1,3-addition in intramolecular approach.
Scheme 12: Linear and angularly fused isomers can be obtained upon intramolecular 1,3-addition.
Scheme 13: Synthesis of α-cedrene via diastereoselective meta photocycloaddition.
Scheme 14: Asymmetric meta photocycloaddition introduced by chirality of tether at position 2.
Scheme 15: Enantioselective meta photocycloaddition in β-cyclodextrin cavity.
Scheme 16: Vinylcyclopropane–cyclopentene rearrangement.
Scheme 17: Further diversification possibilities of the meta photocycloaddition product.
Scheme 18: Double [3 + 2] photocycloaddition reaction affording fenestrane.
Scheme 19: Total synthesis of Penifulvin B.
Scheme 20: Towards the total synthesis of Lacifodilactone F.
Scheme 21: Regioselectivity of ortho photocycloaddition in polarized intermediates.
Scheme 22: Exo and endo selectivity in ortho photocycloaddition.
Scheme 23: Ortho photocycloaddition of alkanophenones.
Scheme 24: Photocycloadditions to naphtalenes usually in an [2 + 2] mode [79].
Scheme 25: Ortho photocycloaddition followed by rearrangements.
Scheme 26: Stable [2 + 2] photocycloadducts.
Scheme 27: Ortho photocycloadditions with alkynes.
Scheme 28: Intramolecular ortho photocycloaddition and rearrangement thereof.
Scheme 29: Intramolecular ortho photocycloaddition to access propellanes.
Scheme 30: Para photocycloaddition with allene.
Scheme 31: Photocycloadditions of dianthryls.
Scheme 32: Photocycloaddition of enone with benzene.
Scheme 33: Intramolecular photocycloaddition affording multicyclic compounds via [4 + 2].
Scheme 34: Photocycloaddition described by Sakamoto et al.
Scheme 35: Proposed mechanism by Sakamoto et al.
Scheme 36: Photocycloaddition described by Jones et al.
Scheme 37: Proposed mechanism for the formation of benzoxepine by Jones et al.
Scheme 38: Photocycloaddition observed by Griesbeck et al.
Scheme 39: Mechanism proposed by Griesbeck et al.
Scheme 40: Intramolecular photocycloaddition of allenes to benzaldehydes.
