US EPA

8722626 

Journal Article 

Alkyl-Alkyl suzuki cross-couplings of unactivated secondary alkyl halides at room temperature 

Saito, B; Fu, GC 

2008 

21 

8 

308-309 

English 

Cross-couplings of primary alkyl electrophiles have been widely discussed in the literature; however, the development of a method to couple unactivated secondary electrophiles remains a challenge. In this report, the investigators used a nickel-based catalyst with a 1,2-diamine ligand for Suzuki cross-couplings of unactivated secondary alkyl halide with alkylboranes at room temperature. Screen tests on different ligands led to trans-N,N'-dime-thyl-l,2- cyclohexanediamine in tandem with bromocyclohexane and 9-BBN alkyl derivative as the best alternative to these cross-coupling reactions (Scheme 1). The method was effectively applied to a wide range of unactivated secondary alkyl bromides, including cyclic, acylic, and bicyclic bromides. The same condition has also been extended to secondary alkyl iodides, primary bromides, and primary iodides with reasonable yields ranging from 68% to 98%. 2008 Data Trace Publishing Company.