20252-71-5Relevant academic research and scientific papers
Regioselective radical amino-functionalizations of allyl alcohols via dual catalytic cross-coupling
Zhang, Zuxiao,Ngo, Duong T.,Nagib, David A.
, p. 3473 - 3477 (2021/04/06)
The regioselective amination and cross-coupling of a range of nucleophiles with allyl alcohols has been enabled by a dual catalytic strategy. This approach entails the combined action of an Ir photocatalyst that enables mild access to N-radicals via an energy transfer mechanism, as well as a Cu complex that intercepts the ensuing alkyl radical upon cyclization. Merger of this Cu-catalyzed cross-coupling enables a broad range of nucleophiles (e.g., CN, SCN, N3, vinyl, allyl) to engage in radical amino-functionalizations of olefins. Notably, stereo, regio, and kinetic probes provide insights into the nature of this Cu-based radical interception.
Catalytic Alkene Difunctionalization via Imidate Radicals
Nakafuku, Kohki M.,Fosu, Stacy C.,Nagib, David A.
, p. 11202 - 11205 (2018/09/12)
The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.
Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols
Trose, Michael,Lazreg, Fa?ma,Lesieur, Mathieu,Cazin, Catherine S. J.
, p. 9910 - 9914 (2015/11/03)
The reaction between nitriles and aminoalcohols to access 2-substituted oxazolines was investigated. Using copper-NHC complexes, various nitriles were successfully converted into the corresponding oxazolines, under milder and less wasteful conditions than those of previously reported methods.
Transition metal and base free synthesis of 2-aryl-2-oxazolines from aldehydes and β-amino alcohols catalysed by potassium iodide
Uma Maheswari,Sathish Kumar,Venkateshwar
, p. 39897 - 39900 (2015/02/18)
Synthesis of 2-aryl-2-oxazolines from β-amino alcohols and aldehydes was achieved in good to excellent yield by employing a potassium iodide (KI)-tert-butyl hydroperoxide (TBHP) catalytic system. This protocol is very mild, metal and base free and can be performed under ambient reaction conditions. This oxidative cyclization strategy was further extended for the synthesis of optically active 2-oxazolines, which can act as very useful chiral auxiliaries and as ligands. This journal is
Nickel-catalyzed decyanation of inert carbon-cyano bonds
Patra, Tuhin,Agasti, Soumitra,Akanksha,Maiti, Debabrata
, p. 69 - 71 (2013/02/21)
Nickel catalyzed decyanation of aryl and aliphatic cyanides with hydrosilane as the hydride source has been developed. This method is easy to handle, scalable and can be carried out without a glove box. The method has been applied in the cyanide directed functionalization reaction and α-substitution of benzyl cyanide.
Ni-catalyzed reduction of inert C-O bonds: A new strategy for using aryl ethers as easily removable directing groups
Alvarez-Bercedo, Paula,Martin, Ruben
, p. 17352 - 17353 (2011/02/23)
An efficient Ni-catalyzed protocol for the reductive cleavage of inert C-O bonds has been developed. The method is characterized by its simplicity and wide scope, thereby allowing the use of aryl ethers as easily removable directing groups in organic synthesis.
Catalytic synthesis of β3-amino acid derivatives from α-amino acids
Byrne, Christopher M.,Church, Tamara L.,Kramer, John W.,Coates, Geoffrey W.
, p. 3979 - 3983 (2008/12/23)
(Chemical Equation Presented) α goes to β! The catalytic ring-expansive carbonylation of oxazolines, easily derived from α-amino acids, to yield β-amino acid derivatives is described. The catalyst is [HCo(CO)4]; high yields are observed for mos
Efficient oxidative synthesis of 2-oxazolines
Schwekendiek, Kirsten,Glorius, Frank
, p. 2996 - 3002 (2008/02/10)
New methodology for the synthesis of variously substituted 2-oxazolines and one dihydrooxazine using aldehydes, amino alcohols, and N-bromosuccinimide as an oxidizing agent is described. This one-pot synthesis is characterized by mild reaction conditions, broad scope, high yields, and its preparative simplicity. Georg Thieme Verlag Stuttgart.
An efficient, eco-friendly, one-pot protocol for the synthesis of 2-oxazolines promoted by ionic liquid/indium chloride
Kamakshi,Reddy, Boreddy S.R.
, p. 463 - 467 (2007/10/03)
2-Oxazolines have been synthesized using a solventless ionic liquid melt in good yields at ambient temperatures. The efficiency of various Lewis acid catalysts for the same reaction has been compared. The effectiveness of different alkyl chains in the ionic liquids for the synthesis of oxazolines has been studied and a butylmethylimidazolinium chloride/indium chloride melt has been found to be the best media for promoting the reaction. CSIRO 2006.
