Ni-catalyzed enantioselective synthesis of β-aminoboronates via spin-center shift and proton transfer
Year: 2025
Type: article
Abstract: The spin-center shift (SCS) process, involving 1,2-radical migrations, plays a pivotal role in both biological transformations and organic synthesis. While the potential of combining SCS with transition metal–catalyzed enantioselective reductive coupling of electrophiles to construct Csp 3 -Csp 3 bonds at remote positions is highly attractive, this strategy has remained unexplored to date. Here, we report an enantioselective Ni-catalyzed reductive cross-coupling for the synthesis of β-aminoboronates. Our catalytic system operates under mild conditions, achieving excellent enantioselectivity while maintaining broad functional group compatibility. Mechanistic studies, including detailed density functional theory (DFT) calculations, demonstrate the synergistic involvement of both SCS and proton transfer (P.T.) processes in the reaction pathway.
Source: Science Advances
Authors: Yahao Wang, Guozhen Wu, Wei Zhu, Xiaotian Qi, Qiuling Song
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $4,500
OpenAlex ID: W4415748378