50777-27-0Relevant academic research and scientific papers
STEREORETENTIVE CROSS-COUPLING OF BORONIC ACIDS
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Paragraph 0112; 0136-0138, (2018/11/21)
The present disclosure provides tri-orthoalkylphenyl phosphine catalysts that are tuned electrically and sterically. Method of using the catalyst for cross-coupling of unactivated secondary boronic acids with near-perfect levels of site- and stereoretention are also provided.
An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence
Aukland, Miles H.,Talbot, Fabien J. T.,Fernández-Salas, José A.,Ball, Matthew,Pulis, Alexander P.,Procter, David J.
supporting information, p. 9785 - 9789 (2018/07/31)
An interrupted Pummerer/nickel-catalysed cross-coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one-pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp-, sp2-, and sp3-hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo- and heterocyclic alkenyl sulfonium salts for cross-coupling.
Highly linear selective cobalt-catalyzed addition of aryl imines to styrenes: Reversing intrinsic regioselectivity by ligand elaboration
Xu, Wengang,Yoshikai, Naohiko
supporting information, p. 14166 - 14170 (2015/02/19)
Highly linear selective, imine-directed hydroarylation of styrene has been achieved with cobalt-based catalytic systems featuring bis(2,4-dimethoxyphenyl)(phenyl)phosphine and either 2-methoxypyridine or DBU as a ligand and a Lewis base additive, respectively, thus affording a variety of 1,2-diarylethanes (bibenzyls) in good yields under mild reaction conditions. The triarylphosphine controls the regioselectivity, while the Lewis base significantly accelerates the reaction. Ligand screening and deuterium-labeling studies provide implications about the roles of the ligand and the Lewis base in the crucial C-C reductive elimination step.
A molecular mechanics approach to mapping the conformational space of diaryl and triarylphosphines
Fey, Natalie,Howell, James A. S.,Lovatt, Jonathan D.,Yates, Paul C.,Cunningham, Desmond,McArdle, Patrick,Gottlieb, Hugo E.,Coles, Simon J.
, p. 5464 - 5475 (2007/10/03)
A molecular mechanics force field has been developed which accurately reproduces experimental solid state structures and conformer interconversion barriers for a series of sterically congested diaryl and triaryl phosphines and some of their chalcogenide and Cr(CO)5 derivatives. The Royal Society of Chemistry 2006.
New entries in Lewis acid-Lewis base bifunctional asymmetric catalyst: Catalytic enantioselective Reissert reaction of pyridine derivatives
Ichikawa, Eiko,Suzuki, Masato,Yabu, Kazuo,Albert, Matthias,Kanai, Motomu,Shibasaki, Masakatsu
, p. 11808 - 11809 (2007/10/03)
The first catalytic enantioselective Reissert reaction of pyridine derivatives that affords products with excellent regio- and enantioselectivity is described. The key for success is the development of new Lewis acid-Lewis base bifunctional asymmetric catalysts containing an aluminum as a Lewis acid and sulfoxides or phosphine sulfides as a Lewis base. These reactions are useful for the synthesis of a variety of chiral piperidine subunits, and catalytic enantioselective formal synthesis of CP-293,019, a selective D4 receptor antagonist, was achieved. Preliminary mechanistic studies indicated that both sulfoxides and phosphine sulfides can activate TMSCN as a Lewis base. In addition, the sulfoxides with appropriate stereochemistry might stabilize a highly enantioselective bimetallic complex (a presumed active catalyst) through internal coordination to aluminum. Copyright
