Shuttle HAT for mild alkene transfer hydrofunctionalization.

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Metal-hydrides, particularly cobalt hydrides (Co-H), are crucial for functionalizing unsaturated carbon-carbon bonds via hydrogen atom transfer (HAT).
• Traditional Co-H generation relies on stoichiometric peroxide oxidants and silane reductants, complicating catalytic processes.

Purpose of the Study:

• To develop a simplified method for generating catalytically active cobalt hydrides (Co-H).
• To introduce a novel catalytic approach termed 'shuttle HAT' that utilizes the reverse process of HAT.

Main Methods:

• The study employs a 'shuttle HAT' strategy, leveraging hydrogen atom abstraction from a C-H bond adjacent to a radical.
• This method generates catalytically active Co-H species without requiring stoichiometric reductant/oxidant mixtures.

Main Results:

• Demonstrated the generality of the shuttle HAT platform across five distinct reaction manifolds.
• Successfully scaled up the reaction to 100 mmol, showcasing its practical applicability.

Conclusions:

• Shuttle HAT offers a streamlined and efficient alternative for generating Co-H species in organic synthesis.
• This methodology significantly simplifies catalytic processes by removing the need for stoichiometric additives.