XPhos

Name: XPhos
Brand: ALDRICH

98%

동의어(들):

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

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크기 선택

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

MDL number:

MFCD04117682

주요 문서

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도움 문의

Quality Level

300

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
Find out more about DOZN™ Scoring

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

SMILES string

CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2

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

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 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.

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.

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

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

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

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

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)

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)

Tetrahedron Letters, 47, 5143-5143 (2006)

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

Quality Level

assay

reaction suitability

greener alternative product score

greener alternative product characteristics

sustainability

mp

functional group

greener alternative category

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InChI

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관련 카테고리

설명

General description

Application

Legal Information

안전성 정보

저장 등급

wgk

flash_point_f

flash_point_c

ppe

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