4436-90-2Relevant academic research and scientific papers
Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones
Liao, Yuan-Xi,Xing, Chun-Hui,Hu, Qiao-Sheng
supporting information; experimental part, p. 1544 - 1547 (2012/06/05)
Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.
Air-assisted addition of grignard reagents to olefins. A simple protocol for a three-component coupling process yielding alcohols
Nobe, Youhei,Arayama, Kyohei,Urabe, Hirokazu
, p. 18006 - 18007 (2007/10/03)
Silylmethyl, tertiary-alkyl, alkenyl, and aryl Grignard reagents underwent intermolecular addition to olefins, such as styrenes, conjugated dienes, and enynes under an air atmosphere to give homologated alcohols. For example, (trimethylsilyl)methylmagnesi
AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.
Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Kolhe, Jayant N.,Newington, Ian M.,Perry, Matthew W. D.
, p. 4235 - 4246 (2007/10/02)
The lithium salts of trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.
Substitution Reactions of Secondary Halides and Epoxides with Higher Order, Mixed Organocuprates, R2Cu(CN)Li2: Synthetic, Stereochemical, and Mechanistic Aspects
Lipshutz, Bruce H.,Wilhelm, Robert S.,Kozlowski, Joseph A.,Parker, David
, p. 3928 - 3938 (2007/10/02)
Higher order cuprates, represented by the general formula R2Cu(CN)Li2, are readily prepared from copper cyanide and 2 equiv of an organolithium.These novel reagents react readily and efficiently with secondary unactivated iodides and bromides affording products of substitution.Likewise, mono-, di-, and trisubstituted epoxides undergo ring opening leading to the corresponding alcohols in excellent yields.The effects of solvent, temperature, gegenion, and variations in ligands are discussed.Replacement of the second equivalent of RLi by CH3Li strongly encouragestransfer of R over CH3 in R(CH3)Cu(CN)Li2 with halides.Use of PhLi as RRLi in place of one RTLi (i.e.RT(Ph)Cu(CN)Li2) is suggested for oxirane cleavage.The stereochemical implications associated with both couplings are also addressed.
