1-Lithio-1,3-dienes as useful building blocks in organic synthesis

Abstract

Both intermolecular reactivities toward C-O and C-N unsaturated substrates and intramolecular reactions of various 1-lithio-1,3-dienes are briefly summarized. Results reveal that intramolecular synergy between the alkenyllithium moiety and the butadienyl skeleton make 1-lithio-1,3-diene derivatives useful and unique as building blocks in organic synthesis. It is demonstrated that substitution patterns and the nature of the substituents on the butadienyl skeleton have remarkable effects on reaction pathways.

Preparation of Thioanisole Biscarbanion and C–H Lithiation/Annulation Reactions for the Access of Five-Membered Heterocycles

“…Carbanion as one of the most reactive species in organic chemistry has continuously been the core synthon in molecular design . Two major strategies are commonly used for the generation of carbanions, including halogen–main group metal exchange and hydrogen–metal exchange (deprotonation). − …”

Construction of Octaalkyl-Substituted and Decasubstituted all-cis-Octatetraenes via Linear Dimerization of 1,4-Dicopper-1,3-butadienes and Subsequent Cross-Coupling with Halides

“…We have been working on the synthesis and synthetic applications of multiply substituted 1-lithio-1,3-butadienes ( I , Scheme ) and 1,4-dilithio-1,3-butadienes ( III ) . The alkyl substituents on the butadienyl skeletons in I and III are all - cis oriented.…”