787618-22-8 Usage
Description
2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl is a bulky phosphine ligand that plays a crucial role in various palladium-catalyzed coupling reactions. Its unique structure allows for enhanced selectivity and reactivity in chemical processes.
Uses
Used in Suzuki Reaction:
2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl is used as a ligand in the palladium-catalyzed coupling of alkyl boronates for the Suzuki reaction. This reaction is a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds.
Used in Cross-Coupling Reactions:
In the field of organic chemistry, 2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl is used as a bulky phosphine ligand for the palladium-catalyzed cross-coupling of aminoethyltrifluoroborates with electron-poor aryl bromides. This application allows for the efficient formation of carbon-carbon bonds in the synthesis of complex organic molecules.
Overall, 2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl is a versatile ligand that significantly contributes to the advancement of palladium-catalyzed coupling reactions in various chemical processes.
Reaction
Versatile Ligand for the Pd-catalyzed coupling of secondary arylamines and alkylamines.
Ligand used for the Pd-catalyzed Negishi cross-coupling reaction of (hetero)arylchlorides.
Synthesis of ladder-type π-conjugated heteroacenes via palladium-catalyzed double N-arylation and intramolecular O-arylation.
A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles,
Versatile ligand used for the Pd-catalyzed C-N coupling reaction of secondary aryl- and alkyl-amines at low temperature with the Pd precatalyst.
Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling of aryl chloride and NHC-boranes.
Ligand for the palladium-catalyzed trifluoromethylation of hindered aryl chlorides.
Ligand used for the palladium-catalyzed coupling of alkyl boronates.
Check Digit Verification of cas no
The CAS Registry Mumber 787618-22-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,8,7,6,1 and 8 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 787618-22:
(8*7)+(7*8)+(6*7)+(5*6)+(4*1)+(3*8)+(2*2)+(1*2)=218
218 % 10 = 8
So 787618-22-8 is a valid CAS Registry Number.
787618-22-8Relevant articles and documents
Development of a scalable palladium-catalyzed α-arylation process for the synthesis of a CGRP antagonist
Desai, Lopa V.,Hay, Michael B.,Leahy, David K.,Wei, Carolyn,Fanfair, Dayne,Rosner, Thorsten,Hsiao, Yi
, p. 5677 - 5684 (2013/07/11)
The Pd-catalyzed α-arylation of cycloheptapyridyl ketone is a key complexity-building step in the synthesis of BMS-846372, a CGRP antagonist. A first-generation process utilized Pd(OAc)2/PtBu 3·HBF4 catalyst system with a strong base NaO tBu. Although this process was demonstrated on multi-kilo scale, the harsh conditions led to non-selective metal catalyzed processes, which generated several operational, quality, and throughput issues. By acquiring detailed knowledge around several important process parameters, we were able to design an efficient and scalable second-generation α-arylation process using a Pd(OAc)2/RuPhos catalyst system with the weaker base, K 3PO4 in tert-amyl alcohol. This new weak base process was high yielding, efficient, and superior in several respects compared to the strong base process. The strategy behind the reaction and isolation development and the process considerations important to scaling a catalytic reaction from laboratory to manufacturing scale will be discussed.