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Platinum-Catalyzed Intramolecular Spirocyclization of -(Methylnaphthalenyl)propiolamides via Formal Aromatic Ene Reaction.
Org Lett
March 2021
Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8550, Japan.
It has been established that an in situ-generated cationic platinum(II)/-BINAP complex catalyzes the intramolecular dearomative 5-endo spirocyclization of -(methylnaphthalenyl)propiolamides via the deprotonation-protonation sequence (formal aromatic ene reaction). Mechanistic studies revealed that our previously reported dearomative 6-endo cyclization followed by the Friedel-Crafts reaction is kinetically and thermodynamically unfavored, and thus, the 5-endo spirocyclization proceeds selectively.
View Article and Find Full Text PDFRegioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.
Org Lett
December 2019
Department of Chemistry , University of Georgia, Athens , Georgia 30602 , United States.
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon.
View Article and Find Full Text PDFCyclic Hypervalent Iodine Reagents: Enabling Tools for Bond Disconnection via Reactivity Umpolung.
Acc Chem Res
December 2018
Laboratory of Catalysis and Organic Synthesis , Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne , Switzerland.
The efficient synthesis of organic compounds is an important field of research, which sets the basis for numerous applications in medicine or materials science. Based on the polarity induced by functional groups, logical bond disconnections can be deduced for the elaboration of organic compounds. Nevertheless, this classical approach makes synthesis rigid, as not all bond disconnections are possible.
View Article and Find Full Text PDFSynthesis of 3,4-Fused Tricyclic Indoles Using 3-Alkylidene Indolines as Versatile Precursors.
Chem Rec
February 2019
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.
In this personal account, our recent studies of novel synthetic methods of 3,4-fused tricyclic indole derivatives using 3-alkylidene indoline derivatives as versatile precursors are discussed. Two types of cascade reactions producing 3,4-fused tricyclic 3-alkylidene indolines were developed based on a palladium-catalyzed intramolecular Heck insertion to an allene-allylic amination cascade and a platinum-catalyzed intramolecular Friedel-Crafts type C-H coupling-allylic amination cascade. Furthermore, three types of 3,4-fused tricyclic indoles were accessible from a single 3-alkylidene indoline precursor via acid-promoted olefin isomerization or oxidative treatments.
View Article and Find Full Text PDFPlatinum-Catalyzed Reactions of 2,3-Bis(diisopropylsilyl)thiophene with Alkynes.
ACS Omega
November 2017
Professor Emeritus Hiroshima University, Higashi-Hiroshima 739-8527, Japan.
The reactions of 2,3-bis(diisopropylsilyl)thiophene () with diphenylacetylene, phenylacetylene, trimethylsilylacetylene, and mesitylacetylene have been reported. The reactions of with diphenylacetylene and phenylacetylene in the presence of a catalytic amount of tetrakis(triphenylphosphine)platinum(0) at 80 °C gave [1,4]disilino[2,3-]thiophene derivatives. With trimethylsilylacetylene, afforded two types of products arising from sp-hybridized C-H bond activation of the acetylene, together with [1,3]disilolo[4,5-]thiophene derivatives.
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