58686-71-8Relevant articles and documents
Consecutive Three-Component Coupling-Addition Synthesis of β-Amino Enoates and 3-Hydroxypyrazoles via Ethyl 3-Arylpropiolates
Niedballa, Jonas,Reiss, Guido J.,Müller, Thomas J. J.
supporting information, p. 5019 - 5024 (2020/07/24)
Two consecutive three-component syntheses furnishing β-amino enoates or 3-hydroxypyrazoles based upon the Sonogashira alkynylation of aryl iodides and ethyl propiolate were established in mostly excellent yields. The ethyl 3-arylpropiolate intermediates are Michael systems which are suited for concatenation with conjugate addition or cyclocondensation giving access to libraries of 21 different β-amino enoates and 17 different 3-hydroxypyrazoles. The rotational barrier of β-pyrrolidino enoates was assessed by studying the coalescence of pyrrolidinyl protons in VT-NMR spectra of electronically different substituted derivatives showing that the electronic substituent effect on the aryl group does not affect the height of the rotational barrier. This indicates that the substituents are essentially oriented orthogonally to the plane of the β-pyrrolidino enoates.
Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation
Butcher, Trevor W.,Hartwig, John F.
supporting information, p. 13125 - 13129 (2018/09/25)
Few allylic electrophiles containing two different substituents at a single allyl terminus and none in which one of the two substituents is a heteroatom, have been shown previously to react with iridium catalysts to form substitution products. We report that iridium-catalysts are uniquely suited to form tertiary allylic fluorides enantioselectively by the addition of a diverse range of carbon-centered nucleophiles at the fluorine-containing terminus of 3-fluoro-substituted allylic esters. The products contain tertiary stereogenic centers bearing a single fluorine, which are isosteric with common tertiary stereocenters containing a single hydrogen. Computational studies reveal the principal steric interactions influencing the stability of endo and exo π-allyl intermediates formed from 3,3-disubstituted allylic electrophiles.
Rhodium-catalyzed C(sp2)-H addition of arylboronic acids to alkynes using a boron-based, convertible ortho-directing group
Yamamoto, Takeshi,Ishibashi, Aoi,Suginome, Michinori
supporting information, p. 1169 - 1172 (2017/08/07)
Temporary modification of a boronyl group with pyrazoryl-aniline allowed insertion of arylpropiolates and diphenylacet-ylenes into the o-C-H bond of arylboronic acids in the presence of rhodium catalysts, giving 3,3-diarylacrylates and triarylethene conta
