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761605

Sigma-Aldrich

BrettPhos Pd G3

98%

同義詞:

[(2-二-环己基膦基-3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯基)-2-(2′-氨基-1,1′-联苯基)]甲磺酸钯 (II) 甲磺酸酯

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About This Item

經驗公式(希爾表示法):
C48H66NO5PPdS
CAS號碼:
分子量::
906.50
MDL號碼:
分類程式碼代碼:
12352300
PubChem物質ID:
NACRES:
NA.22

品質等級

化驗

98%

形狀

solid

特點

generation 3

反應適用性

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: catalyst
core: palladium
reaction type: Cross Couplings

mp

150-193 °C (decomposition)

官能基

amine

SMILES 字串

CS(=O)(O[Pd]c1c(c2c(N)cccc2)cccc1)=O.COc3c(P(C4CCCCC4)C5CCCCC5)c(c6c(C(C)C)cc(C(C)C)cc6C(C)C)c(OC)cc3

InChI

1S/C35H53O2P.C12H10N.CH4O3S.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h19-25,27-28H,9-18H2,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI 密鑰

PQYBJDCHLVJYSD-UHFFFAOYSA-M

一般說明

BrettPhos Pd G3是第三代(G3)Buchwald预催化剂。它具有空气、水分和热稳定性,可溶于多种常见有机溶剂。它在溶液中的使用寿命很长。BrettPhos Pd G3是Buchwald-Hartwig交叉偶联反应的优异试剂。其独有特征包括催化剂负载量低、反应时间短、有效形成催化物质以及精确控制配体:钯比率。

應用

BrettPhos Pd G3可用于单取代脲和1,2二卤代芳族体系之间的C-N偶联反应,生成苯并咪唑酮。
可用于合成下列化合物:
  • 与[(肉桂基)PdCl]2和AgOTf反应生成[Pd(肉桂基)(BrettPhos)]OTf。
  • 与[(巴豆基)PdCl]2和AgOTf反应生成[Pd(巴豆基)(BrettPhos)]OTf。
  • 与[(烯丙基)PdCl]2和AgOTf反应生成[Pd(烯丙基)(BrettPhos)]OTf。
  • 与[(烯丙基)PdCl]2反应生成Pd(烯丙基)(BrettPhos)Cl。
对于小规模和高通量用途,产品为ChemBeads(928321

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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存取文件庫

Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas.
Ernst JB, et al.
Organic Letters, 16(14), 3844-3846 (2014)
Generating Active ?L-Pd (0)? via Neutral or Cationic Π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions.
DeAngelis AJ, et al.
The Journal of Organic Chemistry, 80(13), 6794-6813 (2015)
2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

文章

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

套件中的預成型催化劑是穩定的,但在活化時會變得對空氣敏感;Schlenk 技術有助於擴展規模。

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

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相關內容

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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