Wheel of Baylis-Hillman Reactions

The excellence of Baylis-Hillman reactions!


Depending on the nature of the EWG (electron withdrawing group, the Michael acceptor) and carbonyl compound (the electrophile), many variations of the Baylis–Hillman reaction (aka the Morita–Baylis–Hillman reaction) exist, e.g., for X = NR, it is the aza-Baylis–Hillman reaction.



Wheel of Baylis-Hillman reactions: Click/tap to enlarge the image


EWGs (on the infographic):

  1. oxo-
  2. alkoxycarbonyl-
  3. formyl-
  4. carbamoyl-
  5. cyano-
  6. nitro-
  7. phosphonato-
  8. phenylsulfonyl- or related


DABCO = 1,4-Diazabicyclo[2.2.2]octane

DMAP = 4-Dimethylaminopyridine

DBU = 1,8-Diazabicyclo[5.4.0]undec-7-ene

Ph3P = Triphenylphosphine (also used)


What other wheel(s) 🎡 of organic reactions would you like to see ❓Questions❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗


Reference:

Valiulin, R. Organic Chemistry: 100 Must-Know Mechanisms; De Gruyter: Berlin, 2023.

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