Ni-Catalyzed (A + 2B)-Type Reductive Coupling of Electron-Deficient Alkenes and Alkynes through a Selective...

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Developing efficient synthetic routes for complex organic molecules is crucial in chemistry.
• Nickel catalysis offers a versatile platform for novel bond formations.

Purpose of the Study:

• To develop a novel nickel-catalyzed (A + 2B)-type reductive coupling reaction.
• To synthesize diverse α-skipped dienyl esters with high efficiency and selectivity.

Main Methods:

• Utilizing nickel catalysis for the reductive coupling of electron-deficient alkenes and alkynes.
• Employing mechanistic studies to elucidate the reaction pathway.

Main Results:

• Achieved the first (A + 2B)-type reductive coupling of alkenes with alkynes using nickel.
• Generated diverse α-skipped dienyl esters in up to 99% yield with high chemo- and stereoselectivity.
• Demonstrated synthetic utility in late-stage modification of bioactive molecules and development of antibacterial agents.

Conclusions:

• The developed nickel-catalyzed reaction provides an efficient pathway to α-skipped dienyl esters.
• Mechanistic studies reveal a stepwise pathway involving nickelacycle intermediates.
• This methodology holds significant potential for medicinal chemistry and drug development.