Keita Tanaka

ORCID: 0000-0001-9638-1044
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About
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Research Areas
  • Catalytic C–H Functionalization Methods
  • Catalytic Cross-Coupling Reactions
  • Radical Photochemical Reactions
  • X-ray Diffraction in Crystallography
  • Synthesis and Catalytic Reactions
  • Crystallization and Solubility Studies
  • Asymmetric Hydrogenation and Catalysis
  • Fluorine in Organic Chemistry
  • Sulfur-Based Synthesis Techniques
  • Cyclopropane Reaction Mechanisms
  • Oxidative Organic Chemistry Reactions
  • Synthetic Organic Chemistry Methods
  • Crystal Structures and Properties
  • Advanced biosensing and bioanalysis techniques
  • Catalytic Alkyne Reactions
  • Chemical Synthesis and Characterization
  • Photochromic and Fluorescence Chemistry
  • Marine Toxins and Detection Methods
  • Cardiovascular Issues in Pregnancy
  • Carbohydrate Chemistry and Synthesis
  • Axial and Atropisomeric Chirality Synthesis
  • Agriculture Sustainability and Environmental Impact
  • Syphilis Diagnosis and Treatment
  • Meat and Animal Product Quality
  • Animal Genetics and Reproduction

Scripps Research Institute
2015-2023

Tohoku University
2023

Tokyo Women's Medical University
2022

Massachusetts Institute of Technology
2022

The University of Tokyo
2011

Hokkaido University
2010

The pyridyl group has been extensively employed to direct transition-metal-catalyzed C-H activation reactions in the past half-century. typical cyclic transition states involved these cyclometalation processes have only enabled of ortho-C-H bonds. Here, we report that pyridine is adapted meta-C-H benzyl and phenyl ethyl alcohols through engineering distance geometry a directing template. This template takes advantage stronger σ-coordinating recruit Pd catalysts desired site for...

10.1021/acscentsci.5b00312 article EN publisher-specific-oa ACS Central Science 2015-10-16

A quinoline-based ligand was shown to promote palladium-catalyzed β-C(sp(3))-H fluorination for the first time. range of unnatural enantiopure fluorinated α-amino acids were obtained through sequential arylation and subsequent stereoselective from readily available L-alanine.

10.1021/jacs.5b04088 article EN Journal of the American Chemical Society 2015-05-23

Pd-catalyzed C(sp3)-H activation of alcohol typically shows β-selectivity due to the required distance between chelating atom in attached directing group and targeted C-H bonds. Herein we report design a hemilabile which exploits chelation readily removable benzyl ether moiety direct γ- or δ-C-H carbonylation olefination alcohols. The utility this approach is also demonstrated late-stage functionalization β-estradiol rapidly prepare desired analogues that multi-step syntheses with classical methods.

10.1021/jacs.9b08238 article EN Journal of the American Chemical Society 2019-09-13

Bis(trichlorosilyl)phosphine (HP(SiCl3)2, 1) was prepared from [TBA][P(SiCl3)2] ([TBA]2, TBA = tetra-n-butylammonium) and triflic acid in 36% yield. Phosphine 1 is an efficient reagent for hydrophosphination of unactivated terminal olefins under UV irradiation (15-60 min) gives rise to bis(trichlorosilyl)alkylphosphines (RP(SiCl3)2, R (CH2)5CH3, 88%; (CH2)7CH3, 98%; (CH2)2C(CH3)3, 76%; CH2Cy, 93%; (CH2)2Cy, 95%; CH2CH(CH3)(CH2)2CH3, 82%; (CH2)3O(CH2)3CH3, (CH2)3Cl, 83%; (CH2)2SiMe3, 92%;...

10.1021/jacs.2c05248 article EN Journal of the American Chemical Society 2022-08-04

Abstract Currently, meat production involves environmental issues and high costs; one solution to address this may be produce via cell culture. Therefore, there is an urgent demand for the development of culture methods that replace raw materials with food cultured as food. In study, we designed food-grade-Dulbecco’s Modified Eagle’s Medium (FG-DMEM); when cells in FG-DMEM regular DMEM were compared, was no significant difference growth or differentiation. can used research safe meat.

10.1101/2022.03.28.486069 preprint EN bioRxiv (Cold Spring Harbor Laboratory) 2022-03-29

Azophosphines (Ar–N═N–PR2) were prepared from N-aryl-N′-(trimethylsilyl)diazenes (Ar–N═N–SiMe3) and R2PCl by Me3SiCl elimination or oxidation of phosphinohydrazines (Ar–NH–NH–PR2) 2,5-dialkyl-1,4-benzoquinones. underwent 1,3-dipolar cycloaddition with cyclooctyne dimethylacetylene dicarboxylate to give N-heterocyclic iminophosphoranes (NHIPs), which are structurally similar cyclic (alkyl)(amino)carbenes. The reaction is compatible various phosphorus atom substituents including phenyl...

10.1021/acs.inorgchem.2c01844 article EN Inorganic Chemistry 2022-07-29

Photoresponsive systems for site-selective RNA scission have been prepared by combining Lu(III) ions with acridine/azobenzene dual-modified DNA. The modified DNA forms a heteroduplex substrate RNA, and the target phosphodiester linkages in front of acridine residue is selectively activated so that ion rapidly cleaves linkage. Azobenzene introduced adjacent to acts as photoresponsive switch, which triggers upon UV irradiation. A trans isomer azobenzene efficiently suppresses scission, whereas...

10.4061/2011/162452 article EN cc-by Journal of Nucleic Acids 2011-01-01

Remote C-H functionalization of heterocyclic biaryls will be great importance in synthesis and medicinal chemistry. Through adjusting the geometric relationship directing atom target bonds, two new catalytic templates have been developed to enable more hindered ortho-C-H bonds heterobiaryls bearing heteroatom at meta- or para-positions, affording unprecedented site-selectivity. The use template chaperone also overcomes product inhibition renders catalytic. utility this protocol was...

10.1002/anie.202307581 article EN cc-by Angewandte Chemie International Edition 2023-07-20

Abstract The fluorination is performed on α‐amino acid derivatives carrying a broad range of β‐substituents such as aryl, hetaryl, alkyl, and alkynyl groups endowed with various functional groups.

10.1002/chin.201547039 article EN ChemInform 2015-11-01

The structures of ammonium manganese(II) dialuminium tris(phosphate) dihydrate, (NH 4 )MnAl 2 (PO ) 3 ·2H O, and nickel(II) )NiAl were determined using single-crystal diffraction data. title compounds are isotypic to cobalt aluminophosphate, )CoAl O (LMU-3) [Panz et al. (1998). Inorg. Chim. Acta , 269 73–82], in which a three-dimensional network vertex-sharing AlO 5 PO moieties delineate twelve-membered channels ammonium, NH + transition-metal cations ( M = Mn 2+ Ni reside as charge...

10.1107/s2056989023000555 article EN cc-by Acta Crystallographica Section E Crystallographic Communications 2023-01-26

Abstract Remote C−H functionalization of heterocyclic biaryls will be great importance in synthesis and medicinal chemistry. Through adjusting the geometric relationship directing atom target bonds, two new catalytic templates have been developed to enable more hindered ortho ‐C−H bonds heterobiaryls bearing heteroatom at meta ‐ or para ‐positions, affording unprecedented site‐selectivity. The use template chaperone also overcomes product inhibition renders catalytic. utility this protocol...

10.1002/ange.202307581 article EN cc-by Angewandte Chemie 2023-07-20

Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures 1-4 . Towards this goal, developing strategies to activate that are distal from a functional group is essential 4-6 In context, distinguishing remote on adjacent carbon atoms an extraordinary challenge due the lack electronic or steric bias between two positions. Herein, we report design catalytic system leveraging directing template...

10.26434/chemrxiv.8156561.v1 preprint EN 2019-05-21

<p>Site-selective functionalizations of C–H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures<sup>1-4</sup>. Towards this goal, developing strategies to activate that are distal from a functional group is essential<sup>4-6</sup>. In context, distinguishing remote on adjacent carbon atoms an extraordinary challenge due the lack electronic or steric bias between two positions. Herein, we report...

10.26434/chemrxiv.8156561 preprint EN 2019-05-21

Through consecutive selective C–H functionalization at multiple sites, the direct molecular editing of heteroarene carbon-hydrogen (C–H) bonds has potential to grant rapid access into diverse space; a valuable but often challenging venture achieve in medicinal chemistry. Contrasting with electronically-biased heterocyclic bonds, remote benzocyclic on bicyclic aza-arenes are especially difficult differentiate due lack intrinsic steric/electronic biases. careful consideration distance and...

10.33774/chemrxiv-2021-r8zv6 preprint EN cc-by-nc-nd 2021-10-11

Through consecutive selective C–H functionalization at multiple sites, the direct molecular editing of heteroarene carbon-hydrogen (C–H) bonds has potential to grant rapid access into diverse space; a valuable but often challenging venture achieve in medicinal chemistry. Contrasting with electronically-biased heterocyclic bonds, remote benzocyclic on bicyclic aza-arenes are especially difficult differentiate due lack intrinsic steric/electronic biases. careful consideration distance and...

10.26434/chemrxiv-2021-r8zv6 preprint EN cc-by-nc-nd 2021-10-11
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