91230-17-0Relevant academic research and scientific papers
Photoredox/Cobalt Dual-Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight
Cartwright, Kaitie C.,Joseph, Ebbin,Comadoll, Chelsea G.,Tunge, Jon A.
, p. 12454 - 12471 (2020/09/09)
Recently, dual-catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N-acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's utility and further experimentation has provided new insights into the reaction mechanism. These new developments and insights are anticipated to aid in the expansion of photoredox/cobalt dual-catalytic systems.
Direct substitution of hydroxy group of π-activated alcohols with electron-deficient amines using Re2O7 catalyst
Das, Braja Gopal,Nallagonda, Rajender,Ghorai, Prasanta
experimental part, p. 5577 - 5583 (2012/07/31)
The first example of simple Re2O7-catalyzed direct dehydrative coupling between allylic alcohols with electron-deficient amines has been achieved under mild and open flask conditions. The protocol has also been successfully applied t
Calcium-catalyzed direct amination of π-activated alcohols
Haubenreisser, Stefan,Niggemann, Meike
supporting information; experimental part, p. 469 - 474 (2011/04/16)
A calcium-catalyzed direct amination of π-activated alcohols with different nitrogen nucleophiles under very mild reaction conditions is presented. The high reactivity of the calcium catalyst allows for an efficient conversion of secondary and tertiary benzylic and allylic as well as tertiary propargylic alcohols. Nitrogen nucleophiles such as carbamates, tosylamides and anilines are readily alkylated at room temperature.
Gold versus silver-catalyzed intermolecular hydroaminations of alkenes and dienes
Giner, Xavier,Najera, Carmen,Kovacs, Gabor,Lledos, Agusti,Ujaque, Gregori
experimental part, p. 3451 - 3466 (2012/02/04)
Comparative studies about the hydroamination of unactivated alkenes and dienes catalyzed by either cationic gold(I) triphenyl phosphite complexes or silver salts were performed using sulfonamides, anilines and carbamates as nucleophiles. Gold-catalyzed reactions generally, need lower loadings than those carried out with silver salts. Simple alkenes react only with sulfonamides and weak aromatic amines such as p-nitroaniline, whereas for conjugated dienes carbamates can also be used. Carbon-carbon double bond isomerization is observed only with gold similarly to when triflic acid was used, affording mixtures of regioisomeric products in the same cases. Silver-catalyzed hydroaminations failed with terminal alkenes, except with styrenes. Conjugate dienes can be hydroaminated either at 85 °C in toluene or at room temperature in dichloromethane. Non-conjugated 1,4- and 1,5-dienes suffer double hydroamination leading to saturated N-tosylated heterocyclic amines The catalytic cycle for the silver(I)-catalyzed hydroamination process has been computationally analyzed, resembling gold(I)-catalyzed processes, although with some significant differences. Copyright
Novel synthetic method for allylic amination of cyclic allylic ethers using chlorosulfonyl isocyanate
Lee, Sang Hwi,Kim, In Su,Li, Qing Ri,Dong, Guang Ri,Jung, Young Hoon
experimental part, p. 1901 - 1904 (2011/04/25)
The introduction of amines to allylic or benzylic position of cyclic compounds with chlorosulfonyl isocyanate is developed in high to excellent yields. This method provides a novel access to biologically active compounds including the framework of 1-amino
The stereodivergent aziridination of allylic carbamates, amides and sulfonamides
Davies, Stephen G.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Woods, Philip A.
experimental part, p. 6806 - 6813 (2010/09/17)
A stereodivergent protocol for the aziridination of a range of cyclic allylic amine derivatives has been developed. syn-Products can be obtained in >99:1 dr under H-bonded control and anti-products are obtained in >99:1 dr under steric control by judiciou
Chemo- and diastereoselective cyclopropanation of allylic amines and carbamates
Csatayová, Kristína,Davies, Stephen G.,Lee, James A.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
experimental part, p. 8420 - 8440 (2010/12/20)
A highly chemo- and diastereoselective protocol for the cyclopropanation of tertiary allylic amines with Shi's carbenoid [CF3CO 2ZnCH2I] is described. The high levels of diastereoselectivity observed in these reactions may be attributed to chelation of the nitrogen atom to the zinc reagent, which then transfers a methylene unit to the syn-face of the olefin. Furthermore, a stereodivergent protocol for the cyclopropanation of a range of allylic carbamates has been developed, which provides access to both diastereoisomers of the corresponding cyclopropanes with very high levels of diastereoselectivity: cyclopropanation with the Wittig-Furukawa reagent [Zn(CH2I)2] proceeds under chelation control to give the corresponding syn-product, whilst reaction with Shi's carbenoid proceeds under steric control to give the corresponding anti-cyclopropane, in >95:5 dr in both cases.
Zirconium-catalyzed intermolecular hydroamination of unactivated olefins
Yang, Lei,Xu, Li-Wen,Zhou, Wei,Gao, Yue-Hua,Sun, Wei,Xia, Chun-Gu
scheme or table, p. 1167 - 1171 (2009/09/25)
Highly efficient hydroamination reactions of sulfonamides, carboxamides, and carbamates with unactivated olefins catalyzed by simple and inexpensive zirconium salts under mild reaction conditions were presented for the practical preparation of various amines. These processes gave good to excellent yields of the addition products in Markovnikov addition fashion. Georg Thieme Verlag Stuttgart.
Highly efficient and reusable ionic liquids for the catalyzed hydroamination of alkenes with sulfonamides, carbamates, and carboxamides
Yang, Lei,Xu, Li-Wen,Xia, Chun-Gu
experimental part, p. 1969 - 1974 (2009/12/26)
SO3H-Functionalized ionic liquids were found to be efficient and reusable catalysts in the hydroamination of sulfonamides, carboxamides, p-nitroaniline and carbamates with nonactivated alkenes. The hydroamination could be performed on a large scale and the acidic ionic liquid catalyst could be reused successfully. Georg Thieme Verlag Stuttgart.
Heteropoly acids: a green and efficient heterogeneous Br?nsted acidic catalyst for the intermolecular hydroamination of olefins
Yang, Lei,Xu, Li-Wen,Xia, Chun-Gu
, p. 2882 - 2885 (2008/09/21)
Intermolecular hydroamination of non-activated olefins with amides and benzyl carbamate proceeds efficiently in the presence of environmentally benign silicotungstic acid (HSiW) catalyst under mild conditions in air to afford addition products in good to excellent yields.
