6737-42-4 Usage
Description
1,3-Bis(diphenylphosphino)propane, also known as "dppp" or "tBuXPhos", is a bidentate phosphine ligand with a propane backbone and two diphenylphosphino groups attached to the 1,3-positions. It is a versatile and widely used ligand in coordination chemistry due to its steric and electronic properties, which can influence the reactivity and selectivity of various catalytic processes.
Uses
Used in Coordination Chemistry:
1,3-Bis(diphenylphosphino)propane is used as a bidentate ligand for forming complexes with metal ions, such as the complex dichloro(1,3-bis(diphenylphosphino)propane)nickel, which is formed by reacting with nickel(II) chloride.
Used in Kumada Coupling Reaction:
1,3-Bis(diphenylphosphino)propane is used as a catalyst in the Kumada coupling reaction, a cross-coupling reaction between organohalides and Grignard reagents to form carbon-carbon bonds.
Used in Palladium-Catalyzed Reactions:
1,3-Bis(diphenylphosphino)propane acts as a ligand for palladium(II) catalysts, which are useful for the co-polymerization of carbon monoxide and ethylene to produce polyketones.
Used in Heck Reaction:
1,3-Bis(diphenylphosphino)propane is employed in palladium-catalyzed arylation under the Heck reaction, a method for forming carbon-carbon bonds between an alkene and an aryl halide.
Used in Suzuki Reaction:
1,3-Bis(diphenylphosphino)propane serves as a catalyst in the Suzuki reaction, a cross-coupling reaction between an organoboron compound and an organohalide to form carbon-carbon bonds.
Used in Negishi Coupling:
1,3-Bis(diphenylphosphino)propane is used as a catalyst in Negishi coupling reactions, a type of cross-coupling reaction involving organozinc reagents and various electrophiles.
Used in Sonogashira Coupling:
1,3-Bis(diphenylphosphino)propane is employed as a catalyst in Sonogashira coupling reactions, which involve the coupling of terminal alkynes with aryl or vinyl halides to form carbon-carbon bonds.
Check Digit Verification of cas no
The CAS Registry Mumber 6737-42-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,7,3 and 7 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6737-42:
(6*6)+(5*7)+(4*3)+(3*7)+(2*4)+(1*2)=114
114 % 10 = 4
So 6737-42-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2
6737-42-4Relevant articles and documents
Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium
Ling, Liang,Luo, Meiming,Tang, Jinghua,Yuan, Shuqing,Zeng, Xiaoming
, p. 1581 - 1586 (2022/03/14)
We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani
Decarboxylative Phosphine Synthesis: Insights into the Catalytic, Autocatalytic, and Inhibitory Roles of Additives and Intermediates
Jin, Shengfei,Haug, Graham C.,Nguyen, Vu T.,Flores-Hansen, Carsten,Arman, Hadi D.,Larionov, Oleg V.
, p. 9764 - 9774 (2019/10/14)
Phosphines are among the most widely used ligands, catalysts, and reagents. Current synthetic approaches to phosphines are dominated by nucleophilic displacement reactions with organometallic reagents. Here, we report a radical-based approach to phosphines that proceeds by a cross-electrophile coupling of chlorophosphines and redox-active esters. The reaction allows for the synthesis of a broad range of substituted phosphines that were not readily attainable with the present methods. Our experimental and DFT computational studies also clarified the catalytic, autocatalytic, and inhibitory roles of additives and intermediates, as well as the mechanistic details of the photocatalytic and zinc-mediated redox modes that can have implications for the mechanistic interpretation of other cross-electrophile coupling reactions.
Organocatalyzed Reduction of Tertiary Phosphine Oxides
Schirmer, Marie-Luis,Jopp, Stefan,Holz, Jens,Spannenberg, Anke,Werner, Thomas
supporting information, p. 26 - 29 (2016/01/25)
A novel selective catalytic reduction method of tertiary phosphine oxides to the corresponding phosphines has been developed. Notably, the reaction proceeds smoothly with low catalyst loadings of 1-5 mol% even at low temperature (70 C). Under the optimized conditions various phosphine oxides could be selectively reduced and the desired phosphines were usually obtained in excellent yields above 90%. Furthermore, we have developed a one-pot reaction sequence for the preparation of valuable phosphinborane adducts. Simple addition of BH3THF subsequent to the reduction step gave the desired adducts in yields up to 99%.