Looking for highly efficient cross-coupling ligands? - ACS Publications

Looking for highly efficient cross-coupling ligands? Chem. Eng. News , 2012, 90 (22), Outside Back Cover. DOI: 10.1021/cen-09022-ad40. Publication Dat...
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Looking for highly efficient cross-coupling ligands?

Common Applications: Buchwald-Hartwig amination and C-O coupling Suzuki, Negishi, Stille, Hiyama, Sonogashira cross-couplings α-Arylation reaction

New Applications for Buchwald Ligands N-Arylation of secondary amides1 O

X + n-Bu N H

t-Bu

n-Bu (allylPdCl)2

CH3

JackiePhos Cat. No. 731013

X = Cl, OTf, ONf

N

O CH3

t-Bu

87%

Trifluoromethylation of aryl chlorides2 Cl

CF3

Pd 2 (dba)3, TESCF3 BrettPhos Cat. No. 718742

NC

NC 78%

Conversion of aryl and vinyl triflates to bromides and chlorides3

Aldrich® Chemistry is excited to expand our ever growing list of Buchwald ligands. These new air- and moisture-stable ligands promote cross-coupling reactions more efficiently and exhibit improved reactivity compared to other catalytic systems.

OTf

Pd 2 (dba)3, KX

R

t-BuBrettPhos Cat. No. 730998

• • • •

[(cinnamyl)PdCl] 2, CsF

R

White crystalline solids Air- and moisture-stable Thermally stable

• •

Wide functional group tolerance

t-BuBrettPhos Cat. No. 730998

Excellent selectivity and conversion

X

H3CO t Bu 2P i

CH 3O

i

i Pr

CH 3O

OCH 3

Pr

F3C

Oi Pr

CH3O

SPhos 638072

i

PrO

RuPhos 663131

Pr

X

Cy2P

i

Pr

New

JackiePhos 731013 i

t

Pr i

H3CO

i

i

Pr

XPhos 638064

Bu 2P

i

Pr

Pr

i i

Pr

O

(allylPdCl) 2

R

t-BuBrettPhos Cat. No. 730998

Me 70-95%

N OEt

R

+

X = Cl, OTf, ONf

NaNO2

Pd 2 (dba) 3 t-BuBrettPhos Cat. No. 730998

NO2 R 74-98%

References: (1) Hicks, J. D. et al. J. Am. Chem. Soc. 2009, 131, 16720. (2) Cho, E. J. et al. Science 2010, 328, 1679. (3) Shen, X. et al. J. Am. Chem. Soc. 2010, 132, 14076. (4) Watson, D. A. et al. Science 2009, 325, 1661. (5) Maimone, T. J.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 9990. (6) Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 12898.

Pr

t-BuXPhos 638080

For inquiries about bulk quantities, contact [email protected]. ©2012 Sigma-Aldrich Co. LLC. All rights reserved. SIGMA-ALDRICH and ALDRICH are trademarks of Sigma-Aldrich Co. LLC, registered in the US and other countries. Add Aldrich is a trademark of Sigma-Aldrich Co. LLC.

78883_ALD Long Tail Print Ad (C&EN).indd 1

57-84%

Conversion of aryl chlorides and sulfonates to nitroaromatics6

CF3

i Pr

t-BuBrettPhos 730998 Cy2P

CH3O

P

i Pr

New

BrettPhos 718742

CF3

OH Me

X = Br, Cl, I

i Pr

Pr

New

Cy2P

N

+

R

EtO CF3

F R

O-Arylation of ethyl acetohydroximate5

Highly efficient

Cy2P i Pr H3CO

70-95% X = Br, Cl

Conversion of aryl triflates to aryl fluorides4 OTf

Features:

X R

To find out more about these ligands, visit

Aldrich.com/buchwald 78883

5/14/2012 12:00:04 PM