2902-66-1Relevant academic research and scientific papers
Halogenated isophthalamides and dipicolineamides: The role of the halogen substituents in the anion binding properties
Picci, Giacomo,Bazzicalupi, Carla,Coles, Simon J.,Gratteri, Paola,Isaia, Francesco,Lippolis, Vito,Montis, Riccardo,Murgia, Sergio,Nocentini, Alessio,Orton, James B.,Caltagirone, Claudia
supporting information, p. 9231 - 9238 (2020/07/31)
A novel family of amide-based receptors is herein described. Specifically, the role of the halogen substituents at the aryl moieties in the anion binding properties of a series of halogenated isophthalamides and dipicolineamides (L1-L6) was investigated b
Synthesis, Structures, and Properties of Neutral and Radical Cationic S,C,C-Bridged Triphenylamines
Kato, Shin-ichiro,Matsuoka, Takanori,Suzuki, Shuichi,Asano, Motoko S.,Yoshihara, Toshitada,Tobita, Seiji,Matsumoto, Taisuke,Kitamura, Chitoshi
supporting information, p. 734 - 738 (2020/01/31)
A structurally constrained S,C,C-bridged triphenylamine was synthesized, and the corresponding radical cation was obtained as a hexachloroantimonate by chemical oxidation. An X-ray crystallographic analysis revealed an almost planar structure for this rad
Design and synthesis of chiral urea-derived iodoarenes and their assessment in the enantioselective dearomatizing cyclization of a naphthyl amide
Tariq, M.Umair,Moran, Wesley J.
, (2020/10/12)
A novel family of urea-derived chiral iodoarenes was designed and synthesized for use in enantioselective iodine(I/III) catalysis. Their preparation required the development of a bidirectional synthetic strategy. These new chiral iodoarenes were assessed as catalysts in the dearomatizing cyclization of a naphthyl amide and provided moderate yields of product in some cases with low enantioselectivities.
Preparation, structure, and reactivity of bicyclic benziodazole: A new hypervalent iodine heterocycle
Jarvi, Melissa E.,Makitalo, Cody L.,Rohde, Gregory T.,Saito, Akio,Shea, Michael T.,Yoshimura, Akira,Yusubov, Mekhman S.,Zhdankin, Viktor V.
supporting information, p. 1016 - 1020 (2020/05/06)
A new bicyclic organohypervalent iodine heterocycle derivative of benziodazole was prepared by oxidation of 2-iodo-N,N'-diiso-propylisophthalamide with m-chloroperoxybenzoic acid under mild conditions. Single crystal X-ray crystallography of this compound revealed a five-membered bis-heterocyclic structure with two covalent bonds between the iodine atom and the nitrogen atoms. This novel benziodazole is a very stable compound with good solubility in common organic solvents. This compound can be used as an efficient reagent for oxidatively assisted coupling of carboxylic acids with alcohols or amines to afford the corresponding esters or amides in moderate yields.
A peptide bromoiodinane approach for asymmetric bromolactonization
Whitehead, Daniel C.,Fhaner, Matthew,Borhan, Babak
supporting information; experimental part, p. 2288 - 2291 (2011/05/16)
A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology.
Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide
Denmark, Scott E.,O'Connor, Stephen P.
, p. 3375 - 3389 (2007/10/03)
The effect of zinc iodide on the catalytic, enantioselective cyclopropanation of aliylic alcohols is examined with bis(iodomethyl)zinc as the reagent and bis-methanesulfonamide 7 as the catalyst. Significant rate enhancement was observed when 1 equiv of zinc iodide was present, but more importantly, the enantiomeric excess of the product cyclopropane increased from 80% to 89% for the substrate cinnamyl alcohol. Reaction studies and spectroscopic investigations show that this remarkable influence is the result of reagent modification via a Schlenk equilibrium that produces the more reactive and selective species (iodomethyl)zinc iodide.
