62605-95-2Relevant academic research and scientific papers
A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols
Sweeney, Joseph B.,Ball, Anthony K.,Lawrence, Philippa A.,Sinclair, Mackenzie C.,Smith, Luke J.
supporting information, p. 10202 - 10206 (2018/08/06)
The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).
Copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates with sulfonamides
Powell, David A.,Pelletier, Guillaume
, p. 2495 - 2498 (2008/09/19)
A copper triflate/t-BuOOAc-catalyzed amidation of allylic and benzylic acetates has been developed which is suitable for the coupling of a wide variety of functionalized sulfonamide nucleophiles with acetate electrophiles. The methodology allows for the amidation of benzylic substrates which are not further activated by an additional adjacent alkene or alkyne, enabling simple allylic acetates and primary benzylic acetates to be used as reaction partners.
Palladium-catalyzed reactions of N-allylbenzotriazoles with amines and sulfonamides: A facile route to functionalized allylamines and N-allylsulfonamides
Katritzky,Yao,Denisko
, p. 8063 - 8065 (2007/10/03)
A variety of functionalized N-allylamines and N-allylsulfonamides are synthesized by Pd(II)- catalyzed intermolecular amination of the corresponding N-allylbenzotriazoles.
Synthesis of Medium Ring Azacycles via Allene-based Cyclizations: Evaluation of Possible Mechanistic Pathways
Davies, Ian W.,Shaw, Robert W.,Wisedale, Richard,Gallagher, Timothy
, p. 3557 - 3562 (2007/10/02)
Two pathways have been evaluated to account for the I2-mediated cyclisation of the allenic sulfonamides 1a-e based on (i) the steric demands of the allenic unit, and (ii) the ambident reactivity of the sulfonamide anion.The 1,3-disubstituted allenic sulfo
