82275-84-1Relevant academic research and scientific papers
Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation
Shi, Shasha,Yang, Xianyu,Tang, Man,Hu, Jiefeng,Loh, Teck-Peng
, p. 4018 - 4022 (2021/05/26)
Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.
Nickel/Photoredox Dual Catalytic Cross-Coupling of Alkyl and Amidyl Radicals to Construct C(sp3)-N Bonds
Zhou, Shaofang,Lv, Kang,Fu, Rui,Zhu, Changlei,Bao, Xiaoguang
, p. 5026 - 5034 (2021/05/07)
The construction of C(sp3)-N bonds via direct radical-radical cross-coupling under benign conditions is a desirable but challenging approach. Herein, the cross-coupling of alkyl and amidyl radicals to build aliphatic C-N bonds in a concise, mild, and oxid
NAlkylation of tosylamides using esters as primary and tertiary alkyl sources: Mediated by hydrosilanes activated by a ruthenium catalyst
Nishikata, Takashi,Nagashima, Hideo
supporting information; experimental part, p. 5363 - 5366 (2012/07/03)
Select your group: Either a primary or tertiary alkyl group can be selectively introduced onto the nitrogen atom of tosylamides in a ruthenium-catalyzed reaction employing hydrosilanes through a judicious choice in the esters that serve as the alkyl source (see scheme; Ts= 4-toluenesulfonyl). These N-alkylation reactions are useful for construction of naturally occurring azacyclic skeletons. Copyright
RING-CLOSURE REACTIONS. XX. AN EFFICIENT SYNTHESIS OF MANY-MEMBERED AZACYCLOALKANES
Gargano, Patrizia,Mandolini, Luigi
, p. 31 - 34 (2007/10/02)
An efficient cyclization of N-tosyl-ω-bromoalkylamines to N-tosylazacycloalkanes in the presence of a combination of EtOK/K2CO3 in Me2SO solution is described.This base-solvent system permitted the high-dilution conditions favourable to cyclization to be attained with a conveniently high rate of feed of the bifunctional reactants into the reaction medium.Yields are very good for the large rings, and still satisfactory, although significantly lower, for the medium-sized rings.
