638064

Sigma-Aldrich

2-二环己基磷-2′,4′,6′-三异丙基联苯

greener alternative

98%

别名:
XPhos
Empirical Formula (Hill Notation):
C33H49P
CAS号:
分子量:
476.72
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

质量水平

300

测定

98%

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: C-C Bond Formation

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Hiyama Coupling

reagent type: ligand
reaction type: Negishi Coupling

reagent type: ligand
reaction type: Sonogashira Coupling

reagent type: ligand
reaction type: Stille Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

环保替代产品得分

old score: 2
new score: 1
Find out more about DOZN™ Scoring

环保替代产品特性

Waste Prevention
Atom Economy
Use of Renewable Feedstocks
Catalysis
Learn more about the Principles of Green Chemistry.

mp

187-190 °C (lit.)

官能团

phosphine

环保替代产品分类

Re-engineered

SMILES string

CC(C)c1cc(C(C)C)c(c(c1)C(C)C)-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI

1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3

InChI key

UGOMMVLRQDMAQQ-UHFFFAOYSA-N

一般描述

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.
Xphos-[2-二环己基膦基-2′,4′,6′-三异丙基联苯]是一种由Buchwald集团开发的空气稳定的富电子联芳基单膦配体2,以增强在交叉偶联反应过程中提高钯催化的反应性。

应用

用于Pd催化的生成Vindoline的C-15类似物的铃木偶联反应中的配体。
将2-卤代苯胺直接环化成Pd催化的吲哚和色氨酸. 区域规整聚噻吩的合成。
用于TPGS-750-M中更为环保的优选Sonogashira偶联配体。
XPhose可作为配体用于以下反应:
  • 通过钯催化的烷基砜和芳基卤之间的Negishi交叉偶联用于制备官能化的苄基砜。
  • 与预研磨的乙酸钯(II)一起作为芳基氯化物与三丁基芳基锡烷进行Stille交叉偶联形成相应的联芳基化合物的预催化剂。
  • 与氯化铂一起催化末端芳基烷基与硅烷的氢化硅烷化反应以形成官能化的β-(E)-乙烯基硅烷。
Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors
用于深入研究芳烃磺酸酯、芳基卤的钯催化胺化和酰胺化反应的配体。

包装

1, 5, 25, 100, 500 g in glass bottle

法律信息

用途受美国专利7,223,879保护
用法以美国专利 6307087 和 6395916 为准。

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

闪点(F)

Not applicable

闪点(C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

Tetrahedron Letters, 47, 5143-5143 (2006)
Peter D Johnson et al.
The Journal of organic chemistry, 71(20), 7899-7902 (2006-09-26)
Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo- and iodovindolines were prepared in high yield by the reaction of vindoline with N-bromosuccinimide or N-iodosuccinimide, respectively. The study...
Palladium-Catalyzed Stille Cross-Coupling Reaction of Aryl Chlorides using a Pre-Milled Palladium Acetate and XPhos Catalyst System.
Advanced Synthesis & Catalysis, 350(7-8), 957-961 (2008)
Yanxing Jia et al.
The Journal of organic chemistry, 71(20), 7826-7834 (2006-09-26)
One-pot synthesis of indoles by a palladium-catalyzed annulation of ortho-haloanilines and aldehydes has been developed. Coupling of ortho-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85 degrees C], whereas X-Phos is found to be the ligand...
Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized ?-(E)-vinylsilanes from terminal alkynes.
Hamze A, et al.
Journal of Organometallic Chemistry, 693(16), 2789-2797 (2008)
技术文章
A variety of palladium-catalyzed cross-coupling reactions can be run under mild room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.
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Buchwald Phosphine Ligands
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TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.
了解更多
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
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