Nickel(0)-catalyzed cross-coupling of alkyl arenesulfonates with aryl Grignard reagents

Article abstract of DOI:10.1021/jo026449n

The nickel-catalyzed cross-coupling reactions of neopentyl arenesulfonates with arylmagnesium bromides, involving nucleophilic aromatic substitution of alkyloxysulfonyl groups by aryl nucleophiles, take place in high yields. Optimal efficiencies are obtained by adding 3 + 2 equiv of the Grignard reagent to a mixture of dppfNiCl₂ and the sulfonate in refluxing THF. Neopentyl arenesulfonates are useful sources of the electrophilic aryl groups in these transition metal-catalyzed cross-coupling reactions. Aryl sulfonates are inappropriate due to their ambident reactivity under the reaction conditions. This new cross-coupling reaction can be used for the creative elimination of alkyloxysulfonyl groups from aromatic compounds and for the preparation of unsymmetric terphenyls and oligophenyls.

Full text of DOI:10.1021/jo026449n

SUPPORTING INFORMATION
Nickel(0)-Catalyzed Cross-Coupling of Alkyl Arenesulfonates
with Aryl Grignard Reagents
Chul-Hee Cho, Hee-Sung Yun, and Kwangyong Park*
Department of Chemical Engineering, Chung-Ang University, Huksuk-Dong 221, Dongjak-Ku, Seoul
156-756, South Korea
kypark@cau.ac.kr
FAX: 82-2-815-5476
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Table of Contents
Figure S1. 1H NMR spectrum of 1a
Figure S2. 13C NMR spectrum of 1a
Figure S3. 1H NMR spectrum of 1b
Figure S4. 13C NMR spectrum of 1b
Figure S5. 1H NMR spectrum of 1c
Figure S6. 13C NMR spectrum of 1c
Figure S7. 1H NMR spectrum of 1d
Figure S8. 13C NMR spectrum of 1d
Figure S9. 1H NMR spectrum of 1e
Figure S10. 13C NMR spectrum of 1e
Figure S11. 1H NMR spectrum of 1f
Figure S12. 13C NMR spectrum of 1f
Figure S13. 1H NMR spectrum of 1g
Figure S14. 13C NMR spectrum of 1g
Figure S15. 1H NMR spectrum of 1h
Figure S16. 13C NMR spectrum of 1h
Figure S17. 1H NMR spectrum of 1i
Figure S18. 13C NMR spectrum of 1i
Figure S19. 1H NMR spectrum of 3b
Figure S20. 13C NMR spectrum of 3b
Figure S21. 1H NMR spectrum of 3e
Figure S22. 13C NMR spectrum of 3e
Figure S23. 1H NMR spectrum of 3g
Figure S24. 13C NMR spectrum of 3g
Figure S25. 1H NMR spectrum of 3i
Figure S26. 13C NMR spectrum of 3i
Figure S27. 1H NMR spectrum of 3n
Figure S28. 13C NMR spectrum of 3n
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Figure S29. 1H NMR spectrum of 3o
Figure S30. 13C NMR spectrum of 3o
Figure S31. 1H NMR spectrum of 3p
Figure S32. 13C NMR spectrum of 3p
Figure S33. 1H NMR spectrum of 3q
Figure S34. 13C NMR spectrum of 3q
Figure S35. 1H NMR spectrum of 3r
Figure S36. 13C NMR spectrum of 3r
Figure S37. 1H NMR spectrum of 3s
Figure S38. 13C NMR spectrum of 3s
Figure S39. 1H NMR spectrum of 3t
Figure S40. 13C NMR spectrum of 3t
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Figure S1. 1H NMR spectrum of 1a
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Figure S2. 13C NMR spectrum of 1a
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Figure S3. 1H NMR spectrum of 1b
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Figure S4. 13C NMR spectrum of 1b
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Figure S5. 1H NMR spectrum of 1c
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Figure S6. 13C NMR spectrum of 1c
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Figure S7. 1H NMR spectrum of 1d
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Figure S8. 13C NMR spectrum of 1d
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Figure S9. 1H NMR spectrum of 1e
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Figure S10. 13C NMR spectrum of 1e
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Figure S11. 1H NMR spectrum of 1f
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Figure S12. 13C NMR spectrum of 1f
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Figure S13. 1H NMR spectrum of 1g
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Figure S14. 13C NMR spectrum of 1g
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Figure S15. 1H NMR spectrum of 1h
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Figure S16. 13C NMR spectrum of 1h
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Figure S17. 1H NMR spectrum of 1i
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Figure S18. 13C NMR spectrum of 1i
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Figure S19. 1H NMR spectrum of 3b
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Figure S20. 13C NMR spectrum of 3b
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Figure S21. 1H NMR spectrum of 3e
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Figure S22. 13C NMR spectrum of 3e
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Figure S23. 1H NMR spectrum of 3g
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Figure S24. 13C NMR spectrum of 3g
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Figure S25. 1H NMR spectrum of 3i
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Figure S26. 13C NMR spectrum of 3i
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Figure S27. 1H NMR spectrum of 3n
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