suzuki for pdf - sigma-aldrich

INTRODUCING...

❖

ArylboronicAcids

❖

ArylboronicAcid-Pinacol

Esters

❖

Diboron Esters

❖

Transition-Metal

Catalysts

❖

for all your needsOne-Stop Shopping

Products forSuzuki

Coupling

ChemFiles Vol. 1, No. 1 • 2001

Aldrich is pleased to present its complete selection of arylboronic acids, the building blocks of the Suzuki coupling experiment. Most arylboronicacids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of arylboronic acids may contain varying amounts ofthis cyclic anhydride. Fortunately, the acid and the anhydride work equally well in Suzuki coupling reactions, so the two forms are generally regard-ed as equivalent.

Arylboronic Acids

Suzuki Coupling Reagents

For additional technical information, please phone our Technical Services Department at 1-800-231-8327 (USA) or inquire via the Web at www.sigma-aldrich.com.

49,993-5C

4H

4BCIO

2S

5g

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

The synthesis of biaryl compounds via the reaction of aryl halides with arylboronic acids, commonly referred to asSuzuki coupling,1 is an important area of growth in both synthetic and combinatorial methodologies. Of the wide vari-ety of cross-coupling reactions, Suzuki coupling is the most general and widely used. Arylboronic acids are the favoredreagents due to their stability, low toxicity, and limited side reactions in the coupling reaction. This brochure containsa comprehensive selection of arylboronic acids, arylboronic acid pinacol esters, diboron esters, and transition-metal catalysts useful for the Suzuki coupling reaction. New offerings are added monthly, so if you don’tsee the material you need for your research, please call us at 1-800-231-8327. Your new product suggestions, as always,are welcome and appreciated.

43,683-6C

4H

5BO

2S

1g5g

51,405-5C

5H

5BO

3S

1g5g

51,404-7C

6H

5BCl

2O

2

5g25g

43,684-4C

4H

5BO

2S

1g5g

51,219-2C

5H

7BO

2S

1g5g

46,491-0C

4H

5BO

3

1g10g

46,509-7C

6H

2BF

5O

2

5g25g

47,191-7C

6H

5BCl

2O

2

5g25g

49,990-0C

5H

5BO

3S

1g5g

52,410-7C

6H

4BF

3O

2

1g5g

44,520-7C

6H

5BCl

2O

2

5g25g

51,403-9C

6H

5BF

2O

2

5g25g

49,950-1C

6H

5BBr

2O

2

1g5g

49,991-9C

5H

5BO

3S

1g5g

51,231-1C

6H

5BCl

2O

2

5g

46,507-0C

6H

5BF

2O

2

5g25g

51,223-0C

6H

5BClFO

2

5g

51,402-0C

6H

5BF

2O

2

5g25g

47,192-5C

6H

5BF

2O

2

5g25g

46,508-9C

6H

5BF

2O

2

5g25g

44,162-7C

6H

6BBrO

2

1g5g

47,380-4C

6H

6BBrO

2

5g25g

47,079-1C

6H

5BF

2O

2

1g10g

Essential Tools for Today’s Synthetic Chemist

52,401-8C

6H

7BO

2S

1g5g

52,396-8C

6H

7BO

3

1g

41,755-6C

6H

6BFO

2

1g5g

49,992-7C

6H

7BO

3S

5g25g

44,167-8C

6H

6BIO

2

5g25g

52,635-5C

6H

7BO

3S

5g25g

B7,595-6C

6H

6BBrO

2

1g5g

47,193-3C

6H

6BIO

2

5g25g

28,751-2C

6H

8BNO

2

1g5g

44,165-1C

7H

7BO

3

1g5g

44,521-5C

6H

6BClO

2

1g5g

32,510-4C

6H

6BNO

4

1g5g

44,519-3C

7H

6BF

3O

2

1g10g

43,196-6C

7H

7BO

3

1g5g

41,752-1C

6H

6BClO

2

1g10g

41,754-8C

6H

6BClO

2

1g10g

43,203-2C

7H

6BF

3O

2

1g5g

51,301-6C

7H

6BNO

2

1g

51,270-2C

7H

8BBrO

3

5g

51,224-9C

7H

8BClO

3

5g

48,356-7C

7H

8BFO

2

5g25g

43,932-0C

7H

6BF

3O

2

1g..........................$35.005g........................$117.10

43,195-8C

7H

7BO

3

1g5g

45,677-2C

7H

7BO

4

1g10g


A7,175-1C

6H

8BNO

2

5g25g

41,070-5C

6H

8BNO

2

1g5g

P2,000-9C

6H

7BO

2

10g50g

49,999-4C

7H

7BO

4

1g5g

51,786-0C

6H

2BD

5O

2

1g

45,676-4C

7H

7BO

4

1g10g

44,522-3C

6H

6BFO

2

1g10g

44,164-3C

6H

6BFO

2

1g10g

51,012-2C

7H

6BF

3O

3

5g........................$147.00

48,354-0C

7H

8BFO

3

5g25g

52,147-7C

7H

8BNO

4

1g5g

51,013-0C

7H

6BF

3O

3

5g........................$104.00

39,361-4C

7H

9BO

2

1g5g

45,680-2C

7H

9BO

2S

1g5g

39,362-2C

7H

9BO

2

1g10g

51,233-8C

7H

9BO

3

1g10g

51,283-4C

7H

9BO

3

1g10g

39,360-6C

7H

9BO

2

1g5g

48,008-8C

8H

11BO

2

5g25g

49,994-3C

8H

7BO

3

5g

49,953-6C

8H

11BO

2

5g25g

52,356-9C

8H

8BClO

2

1g10g

52,636-3C

8H

11BO

2S

5g25g

44,523-1C

7H

9BO

3

1g5g

51,897-2C

8H

8BFO

2

1g10g

52,367-4C

9H

15BO

2Si

1g5g

44,168-6C

7H

9BO

3

1g10g

51,286-9C

8H

9BO

4

5g25g

48,348-6C

8H

11BO

4

1g10g

N25-7C

10H

9BO

2

5g25g

41,759-9C

7H

9BO

3

1g5g

47,107-0C

8H

5BF

6O

2

5g

48,349-4C

8H

11BO

4

5g25g

48,005-3C

10H

15BO

2

5g25g

51,221-4C

12H

9BO

2S

2

5g

49,995-1C

12H

9BO

3

5g

48,009-6C

8H

11BO

4

5g25g

52,366-6C

9H

15BO

2Si

1g5g

45,552-0C

8H

11BO

3

1g10g

44,163-5C

8H

11BO

3

1g5g

48,350-8C

8H

11BO

2

5g25g

48,013-4C

10H

9BO

2

5g

48,351-6C

8H

11BO

2

5g25g

52,151-5C

10H

15BO

2

5g25g

49,997-8C

8H

7BO

2S

5g25g

51,211-7C

8H

7BO

2S

5g25g

48,011-8C

8H

11BO

4

5g25g

48,345-1C

12H

11BO

2

5g25g

48,014-2C

12H

11BO

3

5g25g

48,353-2C

8H

12BNO

2

5g25g


41,758-0C

8H

9BO

2

1g5g

47,082-1C

8H

9BO

3

5g25g

47,081-3C

8H

9BO

3

5g25g

47,080-5C

8H

9BO

3

5g25g

47,379-0C

8H

9BO

2

5g25g

48,006-1C

8H

11BO

2

5g25g

45,553-9C

8H

11BO

3

1g10g

51,228-1C

9H

13BO

5

5g

52,149-3C

10H

15BO

2

1g

52,404-2C

12H

21BO

3Si

1g5g

52,990-7C

17H

32B

2O

4

1g5g

52,760-2C

18H

34B

2O

4

1g5g

51,368-7C

10H

12BBrO

2

50g

52,989-3C

19H

36B

2O

4

1g5g

52,255-4C

12H

17BO

3

1g5g

52,757-2C

20H

30B

2O

4

1g5g

52,256-2C

12H

17BO

3

1g5g

51,879-4C

14H

21BO

3

1g5g

52,758-0C

26H

34B

2O

4

1g5g

52,754-8C

15H

21BO

4

1g5g

52,756-4C

15H

21BO

4

1g5g

52,257-0C

12H

17BO

3

1g5g

51,877-8C

14H

20BNO

3

1g5g

51,878-6C

13H

19BO

4

1g5g

51,349-0C

13H

17BO

4

5g

51,875-1C

12H

18BNO

2

1g5g

52,755-6C

13H

16BNO

2

1g5g

The synthesis of biaryl compounds via the Suzuki coupling reaction has become more commonplace now that many arylboronic acids are readilyavailable. Several years ago, Miyaura, et al. demonstrated the utility of cyclic pinacol esters of arylboronic acids in Suzuki coupling reactions. 2,3

Aldrich is pleased to offer the following arylboronic acid pinacol esters4 as part of a growing line of products used in the Suzuki coupling reaction.

Arylboronic Acid-Pinacol Esters

51,880-8C

10H

20B

2O

4

1g5g

47,328-6C

12H

8B

2O

4

1g5g

52,568-5C

12H

24B

2O

4

1g5g

47,329-4C

12H

24B

2O

4

1g5g

52,713-0C

20H

32B

2O

4

1g5g

52,716-5C

16H

24B

2O

12

1g5g

52,714-9C

20H

32B

2O

4

1g5g

The following diboron esters are highly versatile reagents that couple with organic triflates2 and halides3 to give the corresponding boronic esters,which are readily converted to arylboronic acids. This route and the subsequent Suzuki coupling reaction can be run under mild conditions, thus per-mitting the use of cyano-,ester-, carbonyl- and nitro-substituted aryl rings. The wide variety of arylboronic acids available via these diboron estersalso makes this class of compounds suitable for solid-phase combinatorial studies.5,6

Diboron Esters


REFERENCES: (1) Miyaura, N. et al. Synth. Commun. 1981, 11, 513. (2) Ishiyama, T. et al. Tetrahedron Lett. 1997,38, 3447. (3) Ishiyama, T. et al. J. Org. Chem. 1995, 60, 7508. (4) Patents pending including WO/98/45265. (5) Pietrre,S.R.; Baltzer, S. Tetrahedron Lett. 1997, 38, 1197. (6) Brown, S.D.; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 6331. (7) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (8) Stanforth, S. Tetrahedron 1998, 54, 263. (9) Miyaura, N.;Suzuki, A. Chem. Rev. 1995, 95, 2457.

Transition-Metal CatalystsA variety of transition-metal catalysts for the Suzukicoupling reaction are available from Aldrich. Themajority of these catalysts are palladium- and nickel-based, typically utilizing phosphine-derived ligands.7-9

47,055-4 [1,1’-Bis(diphenylphosphino)ferrocene]dichloronickel(II), 97% 1g

37,967-0 [1,1’-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), Complex with CH

2Cl

2

1g; 5g

40,323-7 Dichlorobis(tricyclohexylphosphine)palladium(II), 95% 1g

45,304-8 Dichlorobis(tri-o-tolylphosphine)palladium(II), 97% 1g; 5g

20,867-1 Dichlorobis(triphenylphosphine)palladium(II), 98% 1g; 5g; 25g

41,274-0 Dichlorobis(triphenylphosphine)palladium(II), 99.99% 250mg; 1g

20,586-9 Palladium(II) acetate, 98% 1g; 2g; 10g

37,987-5 Palladium(II) acetate, 99.98%1g; 5g

21,666-6 Tetrakis(triphenylphosphine)palladium(0), 99% 1g; 5g; 25g

32,877-4 Tris(dibenzylideneacetone)dipalladium(0) 500mg; 5g

36,631-5 Tris(dibenzylideneacetone)dipalladium(0)-Chloroform adduct 250mg; 1g

Cyclic Aryl-Substitued

Amino AcidDerivativesAromatic a-substituted proline analogs and g-substi-

tuted pyroglutamates are valuable building blocks in

both medicinal and peptide chemistry. Through

Suzuki coupling technology, they can be used as start-

ing materials in the conversion of aryl bromide deriv-

atives into biaryl compounds. These products have

also found uses in peptide chemistry for the introduc-

tion of diversity and structural constraints in pep-

tidomimetics.

58147 BOC-α-allyl-DL-proline 500mg 52969 BOC-α-benzyl-DL-proline 500mg 90682 BOC-α-(2-bromobenzyl)-

DL-proline 500mg 94866 BOC-α-(4-bromobenzyl)-

DL-proline 500mg90683 BOC-α-(2-chlorobenzyl)-

DL-proline 500mg 90684 BOC-α-(3-chlorobenzyl)-

DL-proline 500mg 30763 BOC-α-(diphenylmethyl)-

DL-proline 500mg 74082 BOC-α-(4-fluorobenzyl)-

DL-proline 500mg 68691 BOC-α-methyl-DL-proline 500mg 76501 BOC-α-(4-methylbenzyl)-

DL-proline 500mg 36748 BOC-α-(1-naphthylmethyl)-

DL-proline 500mg 95566 BOC-α-propyl-DL-proline 500mg 92392 (4R)-BOC-4-benzyl-L-

pyroglutamic acid 500mg 51747 (4R)-BOC-4-benzyl-L-

pyroglutamic acid benzyl ester 500mg 74624 (4R)-BOC-4-(2-bromobenzyl)-

L-pyroglutamic acid benzyl ester 500mg

53371 (4R)-BOC-4-(4-bromobenzyl)-


59703 (4R)-BOC-4-(4-methylbenzyl)-


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suzuki for pdf - sigma-aldrich

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