Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics
- Kevin Lafaye,
- Cyril Bosset,
- Lionel Nicolas,
- Amandine Guérinot and
- Janine Cossy
Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241
Graphical Abstract
Figure 1: Some ruthenium catalysts for metathesis reactions.
Scheme 1: Decomposition of methylidenes 1 and 2.
Scheme 2: Deactivation of G-HII in the presence of ethylene.
Scheme 3: Reaction between GI/GII and n-BuNH2.
Scheme 4: Reaction of GII with amines a–d.
Scheme 5: Amine-induced decomposition of GII methylidene 2.
Scheme 6: Amine-induced decomposition of GII in RCM conditions.
Scheme 7: Deactivation of methylidene 2 in the presence of pyridine.
Scheme 8: Reaction of G-HII with various amines.
Scheme 9: Formation of olefin 22 from styrene.
Scheme 10: Hypothetic deactivation pathway of G-HII.
Scheme 11: RCM of dienic pyridinium salts.
Scheme 12: Synthesis of polycyclic scaffolds using RCM.
Scheme 13: Enyne ring-closing metathesis.
Scheme 14: Synthesis of (R)-(+)-muscopyridine using a RCM strategy.
Scheme 15: Synthesis of a tris-pyrrole macrocycle.
Scheme 16: Synthesis of a bicyclic imidazole.
Scheme 17: RCM using Schrock’s catalyst 44.
Scheme 18: Synthesis of 1,6-pyrido-diazocine 46 by using a RCM.
Scheme 19: Synthesis of fused pyrimido-azepines through RCM.
Scheme 20: RCM involving alkenes containing various N-heteroaromatics.
Scheme 21: Synthesis of dihydroisoquinoline using a RCM.
Scheme 22: Formation of tricyclic compound 59.
Scheme 23: RCM in the synthesis of normuscopyridine.
Scheme 24: Synthesis of macrocycle 64.
Scheme 25: Synthesis of macrocycles possessing an imidazole group.
Scheme 26: Retrosynthesis of an analogue of erythromycin.
Scheme 27: Retrosynthesis of haminol A.
Scheme 28: CM involving 3-vinylpyridine 70 with 71 and vinylpyridine 70 with 73.
Scheme 29: Revised retrosynthesis of haminol A.
Scheme 30: CM between 78 and crotonaldehyde.
Scheme 31: Hypothesized deactivation pathway.
Scheme 32: CM involving an allyl sulfide containing a quinoline.
Scheme 33: CM involving allylic sulfide possessing a quinoxaline or a phenanthroline.
Scheme 34: CM between an acrylate and a 2-methoxy-5-bromo pyridine.
Scheme 35: Successful CM of an alkene containing a 2-chloropyridine.
Scheme 36: Variation of the substituent on the pyridine ring.
Scheme 37: CM involving alkenes containing a variety of N-heteroaromatics.
