期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 12, 页码 4455-4464出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja1097918
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资金
- U.S. Department of Energy (Office of Basic Energy Sciences) [DE-FG02-08ER 15997]
- ACS Division of Organic Chemistry
- Novartis
This paper presents a detailed investigation of the factors controlling site selectivity in the Pd-mediated oxidative coupling of 1,3-disubstituted and 1,2,3-trisubstituted arenes (aryl -H) with cyclometalating substrates (L similar to C-H). The influence of both the concentration and the steric/electronic properties of the quinone promoter are studied in detail. In addition, the effect of steric/electronic modulation of the carboxylate ligand is discussed. Finally, we demonstrate that substitution of the carboxylate for a carbonate X-type ligand leads to a complete reversal in site selectivity for many arene substrates. The origins of these trends in site selectivity are discussed in the context of the mechanism of Pd-catalyzed oxidative cross-coupling.
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