XPhos

Name: XPhos
Brand: ALDRICH

98%

동의어(들):

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

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제품정보 (DICE 배송 시 비용 별도)

실험식(Hill 표기법):

C₃₃H₄₉P

CAS 번호:

564483-18-7

Molecular Weight:

476.72

NACRES:

NA.22

PubChem Substance ID:

24882906

UNSPSC Code:

12352103

주요 문서

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도움 문의

assay

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

greener alternative product score

old score: 2
new score: 1
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greener alternative product characteristics

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

sustainability

Greener Alternative Product

mp

187-190 °C (lit.)

functional group

phosphine

greener alternative category

, Re-engineered

Quality Level

300

General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Atom Economy”, “Use of Renewable Feedstock” and “Enhanced Catalytic Activity”. Click here to view its DOZN scorecard.

XPhos [2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable electron-rich biaryl monophosphine ligand² developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Application

Ligand for increased scope of Pd-catalyzed amination and amidation via arene sulfonates, aryl halides.

Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.
Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd. Synthesis of regioregular polythiophenes.

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

For small scale and high throughput uses, product is also available as ChemBeads (928364)

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

XPhos may be used as a ligand in the following reactions:

Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.
Along with pre-milled palladium(II) acetate as a pre-catalyst for the Stille cross-coupling of aryl chlorides with tributylarylstannanes to form the corresponding biaryl compounds.
Along with platinum chloride to catalyze the hydrosilylation of terminal arylalkynes with silanes to form functionalized β-(E)-vinylsilanes.

Legal Information

Usage subject to US Patent 7,223,879

Usage subject to US Patents 6307087 and 6395916.

저장 등급

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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문서 라이브러리 방문

Tetrahedron Letters, 47, 5143-5143 (2006)

Synthesis of C-15 vindoline analogues by palladium-catalyzed cross-coupling reactions.

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

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)

Palladium-catalyzed, modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes.

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

Suzuki-Miyaura coupling of NHC-boranes: a new addition to the C-C coupling toolbox.

Julien Monot et al.

Organic letters, 11(21), 4914-4917 (2009-10-06)

Complexes of triaryl- and trialkylboranes with N-heterocyclic carbenes (NHCs) participate in Suzuki-Miyaura cross-coupling reactions and provide coupled products in good yields under base-free conditions. The reaction can be applied to Csp(2)-Csp(2) and Csp(2)-Csp(3) carbon-carbon bond formation with triflates, iodides, bromides

모든 관련된 서류 보기

문서

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald Phosphine Ligands

1-tBu-Indenyl Supported Palladium Precatalysts for Cross-Coupling

The Hazari group has developed an improved palladium precatalyst scaffold for a wide range of cross-coupling reactions

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

모두 보기

프로토콜

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

XPhos

98%

크기 선택

제품정보 (DICE 배송 시 비용 별도)

주요 문서

속성

assay

reaction suitability

greener alternative product score

greener alternative product characteristics

sustainability

mp

functional group

greener alternative category

Quality Level

관련 카테고리

설명

General description

Application

Legal Information

안전성 정보

저장 등급

wgk

flash_point_f

flash_point_c

ppe

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