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

DOI: 10.1021/jo026449n

Source and publish data:

Journal of Organic Chemistry p. 3017 - 3025 (2003)

Update date:2022-08-03

Topics:

Authors:

Cho, Chul-Hee

Yun, Hee-Sung

Park, Kwangyong

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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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S20

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S24

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S26

S27

S28

S29

S30

S31

- S2-

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

- S4 -

Figure S2. ¹³C NMR spectrum of 1a

- S5 -

Figure S3. ¹H NMR spectrum of 1b

- S6 -

Figure S4. ¹³C NMR spectrum of 1b

- S7 -

Figure S5. ¹H NMR spectrum of 1c

- S8 -

Figure S6. ¹³C NMR spectrum of 1c

- S9 -

Figure S7. ¹H NMR spectrum of 1d

- S10 -

Figure S8. ¹³C NMR spectrum of 1d

- S11 -

Figure S9. ¹H NMR spectrum of 1e

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Figure S10. ¹³C NMR spectrum of 1e

- S13 -

Figure S11. ¹H NMR spectrum of 1f

- S14 -

Figure S12. ¹³C NMR spectrum of 1f

- S15 -

Figure S13. ¹H NMR spectrum of 1g

- S16 -

Figure S14. ¹³C NMR spectrum of 1g

- S17 -

Figure S15. ¹H NMR spectrum of 1h

- S18 -

Figure S16. ¹³C NMR spectrum of 1h

- S19 -

Figure S17. ¹H NMR spectrum of 1i

- S20 -

Figure S18. ¹³C NMR spectrum of 1i

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Figure S19. ¹H NMR spectrum of 3b

- S22 -

Figure S20. ¹³C NMR spectrum of 3b

- S23 -

Figure S21. ¹H NMR spectrum of 3e

- S24 -

Figure S22. ¹³C NMR spectrum of 3e

- S25 -

Figure S23. ¹H NMR spectrum of 3g

- S26 -

Figure S24. ¹³C NMR spectrum of 3g

- S27 -

Figure S25. ¹H NMR spectrum of 3i

- S28 -

Figure S26. ¹³C NMR spectrum of 3i

- S29 -

Figure S27. ¹H NMR spectrum of 3n

- S30 -

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