Synlett 2018; 29(03): 369-374
DOI: 10.1055/s-0036-1591502
letter
© Georg Thieme Verlag Stuttgart · New York

Iodide-Catalyzed Carbonylation–Benzylation of Benzyl Chlorides with Potassium Aryltrifluoroborates under Ambient Pressure of Carbon Monoxide

Wei Han  *
a   Jiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
b   Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing 210023, P. R. of China   Email: hanwei@njnu.edu.cn
,
Junjie Chen
a   Jiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
,
Fengli Jin
a   Jiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
,
Xiaorong Yuan
a   Jiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road NO.1, Nanjing 210023, P. R. of China
› Author Affiliations

This work was sponsored by the Natural Science Foundation of Jiangsu Province (BK20161553), the Natural Science Foundation of Jiangsu Provincial Colleges and Universities (16KJB150019), the Natural Science Foundation of China (21776139, 21302099), the SRF for ROCS, SEM, the Qing Lan project of Nanjing Normal University, and the Priority Academic Program Development of Jiangsu Higher Education Institutions.
Further Information

Publication History

Received: 27 August 2017

Accepted after revision: 26 September 2017

Publication Date:
26 October 2017 (online)


Abstract

Tetra-N-butylammonium iodide (TBAI) catalyzed carbonylation–benzylation of unactivated benzyl chlorides with potassium aryltrifluoroborates using CO gas has been developed. This reaction is transition-metal free, is carried out under ambient pressure, and provides a wide range of 1,2,3-triarylpropan-1-one derivatives in high yields. The novel method represents a significant improvement over the traditional palladium-catalyzed carbonylation.

Supporting Information