Buchwald precatalyst

Sold under license from MIT, Johnson Matthey offers second and third generation Buchwald catalyst technology at commercial scale for advanced cross coupling applications (1,2). The patented aminobiphenyl scaffold enables rapid and quantitative generation of mono-ligated zero valent Pd-phosphine catalysts upon activation under basic or reducing conditions.
 

Advantages of Buchwald catalysts:

  • Buchwald catalysts are air and moisture-stable and can accommodate a wide range of phosphine ligands: tri-alkyl-phosphines, bi-dentate phosphines, and both early and advanced generation Buchwald ligands.
  • Buchwald catalyst technologies can be applied industrially for a large scope of cross coupling transformations such as Suzuki-Miyaura couplings, Buchwald-Hartwig aminations, Negishi couplings and more (3).
  • Buchwald catalysts activate readily under most cross-coupling conditions, making them suitable for use with low catalyst loading.

Second generation Buchwald precatalysts

XPhos Gen 2
Product number: BPC-201
CAS number: 1310584-14-5
Mol weight: 858.90
Reaction type: Suzuki coupling, Negishi coupling, Heck coupling
SPhos Gen 2
Product number: BPC-203
CAS number: 1375325-64-6
Mol weight: 828.79
Reaction type: Suzuki coupling, Negishi coupling, Heck coupling
RuPhos Gen 2
Product number: BPC-206
CAS number: 1375325-68-0
Mol weight: 798.37
Reaction type: Suzuki coupling, Negishi coupling, Heck coupling
P(tBu)₃ Gen 2
Product number: Pd-168
CAS number: 1375325-71-5
Mol weight: 512.40
Reaction type: Suzuki coupling, Heck coupling, Negishi coupling
XantPhos Gen 2
Product number: Pd-179
CAS number: 1375325-77-1
Mol weight: 888.70
Reaction type: Suzuki coupling, Heck coupling, Buchwald-Hartwig amination
AmPhos Gen 2
Product number: Pd-183 
CAS number: 2169976-34-3
Mol weight: 575.46
Reaction type: Suzuki coupling, Negishi coupling, Kumada coupling
Cy₃P Gen 2
Product number: Pd-185
CAS number: 1353658-81-7
Mol weight: 590.52
Reaction type: Suzuki coupling, Sonogashira coupling, Heck coupling

Third generation Buchwald precatalysts

XPhos Gen 3
Product number: BPC-301
CAS number: 1445085-55-1
Mol weight: 846.46
Reaction type: Suzuki coupling, Negishi coupling, Heck coupling
 
tBuXPhos Gen 3
Product number: BPC-302
CAS number: 1447963-75-8
Mol weight: 882.53
Reaction type: Suzuki coupling, Buchwald-Hartwig amination, Negishi coupling
SPhos Gen 3
Product number: BPC-303 
CAS number: 1445085-82-4
Mol weight: 780.30
Reaction type: Suzuki coupling, Negishi coupling, Heck coupling
 
BrettPhos Gen 3
Product number: BPC-304 
CAS number: 1470372-59-8
Mol weight: 906.50
Reaction type: Buchwald-Hartwig amination, Suzuki coupling, Negishi coupling
tBuBrettPhos Gen 3
Product number: BPC-305 
CAS number: 1536473-72-9
Mol weight: 854.43
Reaction type: Buchwald-Hartwig amination, Suzuki coupling, Negishi coupling
RuPhos Gen 3
Product number: BPC-306 
CAS number: 1445085-77-7
Mol weight: 836.40
Reaction type: Suzuki coupling, Negishi coupling, Heck coupling
 
P(Ad)2(nBu) A Gen 3
Product number: BPC-307 
CAS number: 1651823-59-4
Mol weight: 728.27
Reaction type: Suzuki coupling, Buchwald-Hartwig amination
 
AmPhos Gen 3
Product number: Pd-184 
CAS number: 1820817-64-8
Mol weight: 635.11
Reaction type: Suzuki coupling, Negishi coupling, Kumada coupling
XantPhos Gen 3
Product number: Pd-187 
CAS number: 1445085-97-1
Mol weight: 948.36
Reaction type: Suzuki coupling, Heck coupling, Buchwald-Hartwig amination

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References: 

  1.      1. Bruno, N.C.; Buchwald, S.L. Org. Lett, 2013, 15, 2876 – 2879 
  2.      2. Bruno, N.C.; Tudge, M.T.; Buchwald, S.L. Chem. Sci. 2013, 4, 916 – 920
  3.      3. Bruno, N.C; Niljianskul, N.; Buchwald, S.L. J. Org. Chem. 2014, 79, 4161 – 4166