Nickel‐Catalyzed Boron‐Mediated Saturative Trifunctionalization of Alkynes
Abstract
ABSTRACT Converting simple alkynes into fully substituted alkanes—installing three distinct groups via a sequential one‑pot process—remains a formidable challenge. Herein, we report a boron‐mediated, nickel‐catalyzed strategy that achieves this transformation, enabling the modular assembly of valuable 1,1‐diarylalkanes from both simple alkynyl tetracoordinate borons and N ‐acylglutarimides. The reaction proceeds with high regio‐ and chemoselectivity under mild conditions, exhibiting good functional group tolerance across both coupling partners. Mechanistic studies support a unique reaction pathway involving dual 1,2‐metallate shifts, with water serving as the terminal proton source. The synthetic utility is demonstrated through one‐pot synthesis, late‐stage functionalization of drugs, gram‐scale reactions, and versatile downstream transformations of the products. This strategy represents a distinct strategy that differs from stepwise alkyne reduction, offering a useful disconnection for complex alkane synthesis starting from alkynyl tetracoordinate borons or terminal alkynes via one‑pot borylation.
Article Details
Authors (8)
Shanglin Chen
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources
Yaru Peng
Key Laboratory of Molecule Synthesis and Function Discovery Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources Fuzhou University Fuzhou China
Junmei Lin
Key Laboratory of Molecule Synthesis and Function Discovery Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources Fuzhou University Fuzhou China
Puhui Li
Key Laboratory of Molecule Synthesis and Function Discovery Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources Fuzhou University Fuzhou China
Daojun Ye
College of Materials Science and Engineering Fuzhou University Fuzhou Fujian China
Yuhan Wang
Xingxing Ma
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources
Qiuling Song
Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry, State Key Laboratory of Green and Efficient Development of Phosphorus Resources