700336-74-9Relevant academic research and scientific papers
Catalyzed hydroboration of allyl sulfonamides
Hamilton, Michael G.,Hughes, Catrin E.,Irving, Alison M.,Vogels, Christopher M.,Westcott, Stephen A.
, p. 143 - 147 (2003)
The hydroboration of allyl sulfonamides (4-H3CC6 H4SO2NRCH2CH=CH2: R=H, 1; Ph, 2; Bz, 3) with catecholborane (HBcat) using different rhodium catalysts has been examined using multinuclear NMR spectroscopy. Reactions give complex product distributions, regardless of the choice of catalyst, arising from a competing isomerization reaction. This isomerization reaction can be used with N-substituted allyl sulfonamides 2 and 3 to give the corresponding enamines (4-H3 CC6H4SO2CH=CH2 CH3), which in turn react with HBcat to give regioselective formation of one isomer (4-H3CC6H4 SO2NRCH2CH2(Bcat)CH3).
Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides
Hajiloo Shayegan, Mojtaba,Li, Zhong-Yuan,Cui, Xin
, (2021/12/02)
Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.
A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air
Kundu, Gourab,Rissanen, Kari,Schoenebeck, Franziska,Sperger, Theresa
, p. 21930 - 21934 (2020/10/02)
We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.
Directed carbonylative (3+1+2) cycloadditions of amino-substituted cyclopropanes and alkynes: Reaction development and increased efficiencies using a cationic rhodium system
Shaw, Megan H.,Whittingham, William G.,Bower, John F.
, p. 2731 - 2741 (2016/05/19)
Urea-directed carbonylative insertion of Rh(I)-catalysts into one of the two proximal C-C bonds of aminocyclopropanes generates rhodacyclopentanone intermediates. These are trapped by N-tethered alkynes to provide a (3+1+2) cycloaddition protocol that acc
A new highly chemoselective isomerization of allylamides
Neugnot, Benjamin,Cintrat, Jean-Christophe,Rousseau, Bernard
, p. 3575 - 3579 (2007/10/03)
This work describes the first iridium-catalyzed isomerization of N-allylamides into enamides. This strategy allows the chemoselective preparation of (E)-N-(1-propenyl)-enamides and can be applied for the selective deprotection of N-allylamides.
