Issue in Honor of Prof. Alexandru T. Balaban ARKIVOC 2005 (x) 174-188
Table 11. Examples of migration
Migrating Non-migrating Carbonyl Number of Average Examples of group (R) group (R1) substrate examples Yield, % products 41
2-thienyl 3-thienyl 2-furyl
Me
6 53 O2-benzofuryl
SMe
Me2-benzothienyl O 3-benzothienyl 2-thienyl 3-thienyl OO Ph 2-furyl
5 41 S
Ph
2-benzofuryl Het Ph SMe
2-benzothienyl
11. Conclusions Results compiled and discussed in this short review demonstrate the value of single carboninsertion methods for the homologation of carbonyl compounds in organic synthesis. The benzotriazole-mediated carbon-insertion method described in this review seems to be general, highly regioselective and applicable to most aldehydes and ketones allowing the introduction of a variety of substituents attached to the inserted carbon atom.
References
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