Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 24, Pages 10634-10640Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04670
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Funding
- National Institute of General Medical Sciences of the National Institutes of Health (NIH) [R01GM097243]
- Shanghai Institute of Organic Chemistry (CAS)
- Thermo Q Exactive Plus by NIH [S10OD020022]
- NSF [CHE-1048642]
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While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this challenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% +/- 11% average yield). Mechanistic studies show that Pd strongly prefers the aryl triflate, the Ni catalyst has a small preference for the aryl tosylate, aryl transfer between catalysts is mediated by Zn, and Pd improves yields by consuming arylzinc intermediates.
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