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Synlett 2018; 29(03): 369-374
DOI: 10.1055/s-0036-1591502
DOI: 10.1055/s-0036-1591502
letter
Iodide-Catalyzed Carbonylation–Benzylation of Benzyl Chlorides with Potassium Aryltrifluoroborates under Ambient Pressure of Carbon Monoxide
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.
Key words
benzyl chlorides - carbonylation - potassium aryltrifluoroborates - radicals - synthetic methodsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591502.
- Supporting Information
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For some recent reviews on Pd-catalyzed carbonylations of arylhalides, see:
For recent reviews on carbonylation of C(sp3) halides, see:
Recent reviews on transition-metal-free processes, see:
For reviews, see:
For selected examples of radical carbonylative coupling of alkyl halidesand arylboronic acids (or arylboronic esters), see:
For recent important examples of radical carbonylations of alkyl halides, see: