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

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

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

- S1-

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

…………………………………..

S10

S11

S12

S13

S14

S15

S16

S17

S18

S19

S20

S21

S22

S23

S24

S25

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

…………………………………..

S32

S33

S34

S35

S36

S37

S38

S39

S40

S41

S42

S43

- S3 -

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

- S12 -

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

S21 -

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 -

Products guided by the article

Product name:Benzenesulfonic acid, 4-(1,1-dimethylethyl)-, 2,2-dimethyl-3-phenylpropyl ester

Cas No:524698-44-0

R&D Labs maybe for 524698-44-0

Anhui Dexinjia Biopharm Co., Ltd

Contact:+86-531-82375818

Address:9 Hexie Road, kaifaqu, Taihe
Rayfull Holding Co., Ltd

Contact:+86-577-65618087-605

Address:Room 402, Unit 4 Xinhu Bldg. Waitan Ruian City, Zhejiang China.
Shanghai Synmedia Chemical Co., Ltd

Contact:+86-21-38681880

Address:6th Floor, 11A Building, No.528 Ruiqing Road, Heqing town, Pudong new district, Shanghai China
Shanghai PotentPharm Science and Technology Co.,Ltd

Contact:86-021-51969655

Address:Unit B, Building 18, No.300, Chuantu Rd,Pudong District, Shanghai 201202, China
Zhejiang Linhai Xinhua Chemicals Factory

Contact:0086-13661858911

Address:Xunqiao Development Zone, Linhai, Zhejiang, China

Relevant to this article

Indole naphthyridinones as inhibitors of bacterial enoyl-ACP reductases FabI and FabK

Doi:10.1021/jm0204035
(2003)
Doi:10.1021/ja01510a028
(1959)
Doi:10.1246/bcsj.43.3637
(1970)
A new synthetic route to compounds of the AFDX-type with affinity to muscarinic M₂-receptor

Doi:10.1016/S0040-4020(02)01623-X
(2003)
Doi:10.1246/bcsj.37.1745
(1964)
Aloperine: Stereocontrolled synthesis of two stereoisomers and determination of absolute configuration

Doi:10.1021/jo9621231
(1997)

Article Doi