Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 52, Pages 21891-21898Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c11056
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Funding
- AstraZeneca
- Royal Society
- ERC [757381]
- EPSRC [EP/N005422/1]
- European Research Council (ERC) [757381] Funding Source: European Research Council (ERC)
- EPSRC [EP/N005422/1] Funding Source: UKRI
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Use of attractive noncovalent interactions between ligand and substrate is an emerging strategy for controlling positional selectivity. A key question relates to whether fine control on molecules with multiple, closely spaced reactive positions is achievable using typically less directional electrostatic interactions. Herein, we apply a 10-piece toolkit comprising of two closely related sulfonated phosphine ligands and five bases, each possessing varying cation size, to the challenge of site-selective cross-coupling of multiply chlorinated arenes. The fine tuning provided by these ligand/base combinations is effective for Suzuki-Miyaura coupling and Buchwald-Hartwig coupling on a range of isomeric dichlorinated and trichlorinated arenes, substrates that would produce intractable mixtures when typical ligands are used. This study develops a practical solution for site-selective cross-coupling to generate complex, highly substituted arenes.
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