Gold vinylidene complexes: intermolecular C(sp3)-H insertions and cyclopropanations pathways.

Area of Science:

• Organometallic Chemistry
• Organic Synthesis

Background:

• Gold catalysis is a rapidly growing field in organic synthesis.
• Vinylidene complexes are versatile intermediates in organometallic chemistry.

Purpose of the Study:

• To explore the reactivity of gold vinylidene species in C-H functionalization.
• To develop a novel synthetic route to cyclobutene derivatives.

Main Methods:

• Generation of highly reactive gold vinylidene species.
• Intermolecular C(sp(3))-H insertion reactions into unactivated alkanes.
• Cyclopropanation followed by a ring-enlargement cascade.

Main Results:

• Gold vinylidene species successfully inserted into C(sp(3))-H bonds of unactivated alkanes.
• Alkylidene carbenes were generated in situ from the vinylidene species.
• Cyclobutene derivatives were synthesized in a diastereoselective manner through a one-step cascade reaction.

Conclusions:

• Highly reactive gold vinylidene species are effective for C-H functionalization of alkanes.
• This methodology provides a new pathway for constructing cyclobutene derivatives.
• The reaction proceeds via a cascade mechanism involving cyclopropanation and ring expansion.