Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution
Masahiro Kojima and Shigeki Matsunaga present allyl 4-chlorophenyl sulfone as a versatile 1,1-synthon.
Sulfones are well-known chemical chameleons, namely building blocks that can behave as either nucleophiles or electrophiles depending on how they are activated and reacted. For example, a sulfone can stabilize an adjacent carbanion or alternatively can be displaced by a carbon nucleophile, upon suitable activation. For this reason, some sulfones can be considered as 1,1-dipole synthons. This peculiar reactivity of sulfones continues to attract the interest of organic chemists and represents an invaluable source of new reactions. The story of this SYNTHESIS paper started with a discovery by the group of Professors Masahiro Kojima and Shigeki Matsunaga at Hokkaido University (Japan) in 2018: at that time, they were studying the dual cobalt-photoredox catalysis for allylic alkylation.