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-Alkanes to -alcohols: Formal primary C─H bond hydroxymethylation via quadruple relay catalysis.
Sci Adv
November 2020
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Nature is able to synergistically combine multiple enzymes to conduct well-ordered biosynthetic transformations. Mimicking nature's multicatalysis in vitro may give rise to new chemical transformations via interplay of numerous molecular catalysts in one pot. The direct and selective conversion of abundant -alkanes to valuable -alcohols is a reaction with enormous potential applicability but has remained an unreached goal.
View Article and Find Full Text PDFMethane Borylation Catalyzed by Ru, Rh, and Ir Complexes in Comparison with Cyclohexane Borylation: Theoretical Understanding and Prediction.
J Am Chem Soc
September 2020
Element Strategy Initiative for Catalysts and Batteries, Kyoto University, Goryo-Ohara 1-30, Nishikyo-ku, Kyoto 615-8245, Japan.
Methane borylation catalyzed by Cp*M(Bpin) (M = Ru or Rh; HBpin = pinacolborane; = 2 or 3) and (TMPhen)Ir(Bpin) (TMPhen = 3,4,7,8-tetramethyl-1,10-phenanthroline) was investigated by DFT in comparison with cyclohexane borylation. Because Ru-catalyzed borylation has not been theoretically investigated yet, its reaction mechanism was first elucidated; Cp*Ru(Bpin) is an active species, and Cp*Ru(Bpin)(H)(CH) is a key intermediate. In , the Ru is understood to have an ambiguous oxidation state between +IV and +VI because it has a H··Bpin bonding interaction with a bond order of about 0.
View Article and Find Full Text PDFOxidatively Induced Reductive Elimination: Exploring the Scope and Catalyst Systems with Ir, Rh, and Ru Complexes.
J Am Chem Soc
March 2019
Department of Chemistry , Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141 , South Korea.
Direct conversion of C-H bonds into C-C bonds is a promising alternative to the conventional cross-coupling reactions, thus giving rise to a wide range of efficient catalytic C-H functionalization reactions. Among the elementary stages in the catalytic C-C bond formation, reductive elimination constitutes a key step of the catalytic cycle, and, therefore, extensive studies have been made to facilitate this process. In this regard, oxidation on the metal center of a post-transmetalation intermediate would be an appealing approach.
View Article and Find Full Text PDFTotal Synthesis of α-Tocopherol through Enantioselective Iridium-Catalyzed Fragmentation of a Spiro-Cyclobutanol Intermediate.
Chemistry
April 2019
Department of Chemistry, University of Cologne, Greinstrasse 4, 50939, Koeln, Germany.
A conceptionally new strategy for the asymmetric (2R-selective) synthesis of α-tocopherol (vitamin E) was developed. In the stereocontrolled key step, a prochiral spiro[chromane-2,3'-cyclobutanol] unit is effectively desymmetrized under C-C bond activation in an unprecedented iridium-catalyzed transformation using (S)-DTBM-SegPhos as a chiral ligand (e.r.
View Article and Find Full Text PDFTransition-metal-catalyzed asymmetric allylic dearomatization reactions.
Acc Chem Res
August 2014
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
Dearomatization reactions serve as powerful methods for the synthesis of highly functionalized, three-dimensional structures starting with simple planar aromatic compounds. Among processes of this type, catalytic asymmetric dearomatization (CADA) reactions are attractive owing to the large number of aromatic compounds that are readily available and the fact that they enable direct access to enantiopure polycycles and spirocycles, which frequently are key structural motifs in biologically active natural products and pharmaceuticals. However, as a consequence of their high stabilities, arenes only difficultly participate in dearomatization reactions that take place with high levels of enantioselectivity.
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