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
