Nickel-Catalyzed 1,2-Distyrylation of 3-Buten-1-ol.

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Directing group strategies are crucial for regioselective functionalization.
• Hydroxyl groups can potentially serve as endogenous directing groups.
• Nickel catalysis offers versatile pathways for C-C bond formation.

Purpose of the Study:

• To develop a novel nickel-catalyzed 1,2-distyrylation of 3-buten-1-ol.
• To utilize the hydroxyl group as a native directing group for this transformation.
• To explore the scope and scalability of the developed methodology.

Main Methods:

• Nickel-catalyzed cross-coupling reaction.
• Utilizing 3-buten-1-ol as a substrate with its hydroxyl group directing.
• Employing various alkenyl boronates and styryl iodides.

Main Results:

• First report of nickel-catalyzed 1,2-distyrylation of 3-buten-1-ol.
• Simultaneous incorporation of two distinct styryl groups across a double bond.
• Moderate to good yields of diverse 1,2-distyrylation products achieved.
• Broad functional group compatibility and gram-scale scalability demonstrated.

Conclusions:

• The developed protocol offers an efficient route to 1,2-distyrylation using a native directing group.
• The reaction proceeds under mild conditions with broad substrate scope.
• Mechanistic studies suggest a radical pathway involving a Ni(0)/Ni(I)/Ni(II) catalytic cycle.