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Title: Activation of olefins via asymmetric Bronsted acid catalysis

Abstract

The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Bronsted acidic sites of appropriate strength can protonate olefins and thereby generate carbocations that ultimately react to form natural products. Although chemists have recently designed chiral Bronsted acid catalysts to activate imines and carbonyl compounds, mimicking these enzymes to protonate simple olefins that then engage in asymmetric catalytic reactions has remained a substantial synthetic challenge. Here, we show that a class of confined and strong chiral Bronsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. In conclusion, the methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (–)-Boivinianin A.

Authors:
ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]
+ Show Author Affiliations
  1. Max-Planck-Institut fur Kohlenforschung, Mulheim an der Ruhr (Germany)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Max Planck Institute for Chemical Energy Conversion, Mulheim an der Ruhr (Germany)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Oak Ridge Leadership Computing Facility (OLCF)
Sponsoring Org.:
USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR)
OSTI Identifier:
1454404
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Science
Additional Journal Information:
Journal Volume: 359; Journal Issue: 6383; Journal ID: ISSN 0036-8075
Publisher:
AAAS
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Tsuji, Nobuya, Kennemur, Jennifer L., Buyck, Thomas, Lee, Sunggi, Prevost, Sebastien, Kaib, Philip S. J., Bykov, Dmytro, Fares, Christophe, and List, Benjamin. Activation of olefins via asymmetric Bronsted acid catalysis. United States: N. p., 2018. Web. doi:10.1126/science.aaq0445.
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Tsuji, Nobuya, Kennemur, Jennifer L., Buyck, Thomas, Lee, Sunggi, Prevost, Sebastien, Kaib, Philip S. J., Bykov, Dmytro, Fares, Christophe, & List, Benjamin. Activation of olefins via asymmetric Bronsted acid catalysis. United States. https://doi.org/10.1126/science.aaq0445
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Tsuji, Nobuya, Kennemur, Jennifer L., Buyck, Thomas, Lee, Sunggi, Prevost, Sebastien, Kaib, Philip S. J., Bykov, Dmytro, Fares, Christophe, and List, Benjamin. Fri . "Activation of olefins via asymmetric Bronsted acid catalysis". United States. https://doi.org/10.1126/science.aaq0445. https://www.osti.gov/servlets/purl/1454404.
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@article{osti_1454404,
title = {Activation of olefins via asymmetric Bronsted acid catalysis},
author = {Tsuji, Nobuya and Kennemur, Jennifer L. and Buyck, Thomas and Lee, Sunggi and Prevost, Sebastien and Kaib, Philip S. J. and Bykov, Dmytro and Fares, Christophe and List, Benjamin},
abstractNote = {The activation of olefins for asymmetric chemical synthesis traditionally relies on transition metal catalysts. In contrast, biological enzymes with Bronsted acidic sites of appropriate strength can protonate olefins and thereby generate carbocations that ultimately react to form natural products. Although chemists have recently designed chiral Bronsted acid catalysts to activate imines and carbonyl compounds, mimicking these enzymes to protonate simple olefins that then engage in asymmetric catalytic reactions has remained a substantial synthetic challenge. Here, we show that a class of confined and strong chiral Bronsted acids enables the catalytic asymmetric intramolecular hydroalkoxylation of unbiased olefins. In conclusion, the methodology gives rapid access to biologically active 1,1-disubstituted tetrahydrofurans, including (–)-Boivinianin A.},
doi = {10.1126/science.aaq0445},
journal = {Science},
number = 6383,
volume = 359,
place = {United States},
year = {2018},
month = {3}
}
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https://doi.org/10.1126/science.aaq0445
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Works referenced in this record:

Stronger Brønsted Acids: Recent Progress
journal, July 2015

Generalized Gradient Approximation Made Simple
journal, October 1996

  • Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
  • Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868
  • DOI: 10.1103/PhysRevLett.77.3865

Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization
journal, December 2010

  • Čorić, Ilija; Müller, Steffen; List, Benjamin
  • Journal of the American Chemical Society, Vol. 132, Issue 49
  • DOI: 10.1021/ja108642s

Asymmetric spiroacetalization catalysed by confined Brønsted acids
journal, March 2012

Catalytic Asymmetric Torgov Cyclization: A Concise Total Synthesis of (+)-Estrone
journal, July 2014

  • Prévost, Sébastien; Dupré, Nathalie; Leutzsch, Markus
  • Angewandte Chemie International Edition, Vol. 53, Issue 33
  • DOI: 10.1002/anie.201404909

A survey of Hammett substituent constants and resonance and field parameters
journal, March 1991

  • Hansch, Corwin.; Leo, A.; Taft, R. W.
  • Chemical Reviews, Vol. 91, Issue 2
  • DOI: 10.1021/cr00002a004

Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation
journal, March 2017

  • Gao, Shu-Shan; Garcia-Borràs, Marc; Barber, Joyann S.
  • Journal of the American Chemical Society, Vol. 139, Issue 10
  • DOI: 10.1021/jacs.7b01089

Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes
journal, September 2017

  • Liu, Luping; Kim, Hyejin; Xie, Youwei
  • Journal of the American Chemical Society, Vol. 139, Issue 39
  • DOI: 10.1021/jacs.7b08357

Cobalt-catalyzed oxidative cyclization of gem -disubstituted conjugated alkenols
journal, July 2016

Total Synthesis of (−)-Lepistine
journal, May 2014

  • Kitabayashi, Yusuke; Yokoshima, Satoshi; Fukuyama, Tohru
  • Organic Letters, Vol. 16, Issue 11
  • DOI: 10.1021/ol5010033

The ORCA program system: The ORCA program system
journal, June 2011

  • Neese, Frank
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 1
  • DOI: 10.1002/wcms.81

On some approximations in applications of X α theory
journal, October 1979

  • Dunlap, B. I.; Connolly, J. W. D.; Sabin, J. R.
  • The Journal of Chemical Physics, Vol. 71, Issue 8
  • DOI: 10.1063/1.438728

Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin
journal, November 2015

  • Ruscoe, Rebecca E.; Fazakerley, Neal J.; Huang, Huanming
  • Chemistry - A European Journal, Vol. 22, Issue 1
  • DOI: 10.1002/chem.201504343

Synthesis of oxaspiro[m.n] skeletons based on the Nicholas reaction
journal, April 2002

Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons
journal, January 2000

  • Tu, Yong Q.; Hübener, Achim; Zhang, Hesheng
  • Synthesis, Vol. 2000, Issue 13
  • DOI: 10.1055/s-2000-8232

Ultrahigh-Resolution NMR Spectroscopy
journal, May 2014

  • Foroozandeh, Mohammadali; Adams, Ralph W.; Meharry, Nicola J.
  • Angewandte Chemie International Edition, Vol. 53, Issue 27
  • DOI: 10.1002/anie.201404111

A general practice assessment of mefruside (‘Baycaron’) in the treatment of oedema and hypertension
journal, January 1973

A Brønsted Acid Catalyst for the Enantioselective Protonation Reaction
journal, July 2008

  • Cheon, Cheol Hong; Yamamoto, Hisashi
  • Journal of the American Chemical Society, Vol. 130, Issue 29
  • DOI: 10.1021/ja8041542

Recent advances in metal free- and late transition metal-catalysed hydroamination of unactivated alkenes
journal, January 2015

  • Bernoud, Elise; Lepori, Clément; Mellah, Mohamed
  • Catalysis Science & Technology, Vol. 5, Issue 4
  • DOI: 10.1039/C4CY01716A

Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes
journal, October 2016

  • Kaib, Philip S. J.; Schreyer, Lucas; Lee, Sunggi
  • Angewandte Chemie International Edition, Vol. 55, Issue 42
  • DOI: 10.1002/anie.201607828

Catalytic Synthesis of Saturated Oxygen Heterocycles by Hydrofunctionalization of Unactivated Olefins: Unprotected and Protected Strategies
journal, August 2016

  • Shigehisa, Hiroki; Hayashi, Miki; Ohkawa, Haruna
  • Journal of the American Chemical Society, Vol. 138, Issue 33
  • DOI: 10.1021/jacs.6b05720

Rh-Catalyzed Enantioselective Hydrogenation of Vinyl Boronates for the Construction of Secondary Boronic Esters
journal, May 2006

  • Moran, Wesley J.; Morken, James P.
  • Organic Letters, Vol. 8, Issue 11
  • DOI: 10.1021/ol060735u

Asymmetric Hydroalkoxylation of Non-Activated Alkenes: Titanium-Catalyzed Cycloisomerization of Allylphenols at High Temperatures
journal, February 2015

  • Schlüter, Johannes; Blazejak, Max; Boeck, Florian
  • Angewandte Chemie International Edition, Vol. 54, Issue 13
  • DOI: 10.1002/anie.201409252

Recent developments in alkene hydro-functionalisation promoted by homogeneous catalysts based on earth abundant elements: formation of C–N, C–O and C–P bond
journal, January 2015

  • Rodriguez-Ruiz, Violeta; Carlino, Romain; Bezzenine-Lafollée, Sophie
  • Dalton Transactions, Vol. 44, Issue 27
  • DOI: 10.1039/C5DT00280J

Fully optimized contracted Gaussian basis sets for atoms Li to Kr
journal, August 1992

  • Schäfer, Ansgar; Horn, Hans; Ahlrichs, Reinhart
  • The Journal of Chemical Physics, Vol. 97, Issue 4
  • DOI: 10.1063/1.463096

Brønsted Acid Catalyzed Asymmetric S N 2-Type O-Alkylations
journal, February 2013

  • Čorić, Ilija; Kim, Ji Hye; Vlaar, Tjøstil
  • Angewandte Chemie International Edition, Vol. 52, Issue 12
  • DOI: 10.1002/anie.201209983

Accurate Coulomb-fitting basis sets for H to Rn
journal, January 2006

  • Weigend, Florian
  • Physical Chemistry Chemical Physics, Vol. 8, Issue 9
  • DOI: 10.1039/b515623h

UCSF Chimera?A visualization system for exploratory research and analysis
journal, January 2004

  • Pettersen, Eric F.; Goddard, Thomas D.; Huang, Conrad C.
  • Journal of Computational Chemistry, Vol. 25, Issue 13
  • DOI: 10.1002/jcc.20084

Chiral Lewis Base-Assisted Brønsted Acid (LBBA)-Catalyzed Enantioselective Cyclization of 2-Geranylphenols
journal, June 2011

  • Sakakura, Akira; Sakuma, Masayuki; Ishihara, Kazuaki
  • Organic Letters, Vol. 13, Issue 12
  • DOI: 10.1021/ol201032t

A stereoselective synthesis of trisubstituted alkenes. Part 1. Nickel-catalysed coupling of Grignard reagents with 5-alkyl-2,3-dihydrofurans
journal, January 1992

  • Kocieński, Philip J.; Pritchard, Martin; Wadman, Sjoerd N.
  • J. Chem. Soc., Perkin Trans. 1, Issue 24
  • DOI: 10.1039/P19920003419

A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
journal, April 2010

  • Grimme, Stefan; Antony, Jens; Ehrlich, Stephan
  • The Journal of Chemical Physics, Vol. 132, Issue 15
  • DOI: 10.1063/1.3382344

Asymmetric additions to dienes catalysed by a dithiophosphoric acid
journal, February 2011

  • Shapiro, Nathan D.; Rauniyar, Vivek; Hamilton, Gregory L.
  • Nature, Vol. 470, Issue 7333
  • DOI: 10.1038/nature09723

Copper(I)-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Alkenes
journal, April 2015

Effect of the damping function in dispersion corrected density functional theory
journal, March 2011

  • Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars
  • Journal of Computational Chemistry, Vol. 32, Issue 7
  • DOI: 10.1002/jcc.21759

Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes
journal, June 2015

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Hidden Brønsted Acid Catalysis: Pathways of Accidental or Deliberate Generation of Triflic Acid from Metal Triflates
journal, November 2011

  • Dang, Tuan Thanh; Boeck, Florian; Hintermann, Lukas
  • The Journal of Organic Chemistry, Vol. 76, Issue 22
  • DOI: 10.1021/jo201631x

Preparation of fluorinated 1,2- and .alpha.,.omega.-diols
journal, January 1993

  • Qiu, Weiming; Burton, Donald J.
  • The Journal of Organic Chemistry, Vol. 58, Issue 2
  • DOI: 10.1021/jo00054a027

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System
journal, July 2015

A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis
journal, July 2007

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988

Design of Chiral N -Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels−Alder Reaction
journal, August 2006

  • Nakashima, Daisuke; Yamamoto, Hisashi
  • Journal of the American Chemical Society, Vol. 128, Issue 30
  • DOI: 10.1021/ja062508t

Achiral Pyridine Ligand-Enabled Enantioselective Radical Oxytrifluoromethylation of Alkenes with Alcohols
journal, May 2017

  • Cheng, Yong-Feng; Dong, Xiao-Yang; Gu, Qiang-Shuai
  • Angewandte Chemie International Edition, Vol. 56, Issue 30
  • DOI: 10.1002/anie.201702925

Sesquiterpenoid derivatives from Cipadessa boiviniana (Meliaceae)
journal, April 2006

  • Mulholland, Dulcie A.; McFarland, Kathryn; Randrianarivelojosia, Milijaona
  • Biochemical Systematics and Ecology, Vol. 34, Issue 4
  • DOI: 10.1016/j.bse.2005.11.005

Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations
journal, May 2010

Stereochemical course of the hydrogen migration in the boron trifluoride etherate-catalyzed rearrangement of 1,1-disubstituted epoxides
journal, May 2000

Self-consistent molecular Hartree—Fock—Slater calculations I. The computational procedure
journal, September 1973

CLIP-COSY: A Clean In-Phase Experiment for the Rapid Acquisition of COSY-type Correlations
journal, May 2016

  • Koos, Martin R. M.; Kummerlöwe, Grit; Kaltschnee, Lukas
  • Angewandte Chemie International Edition, Vol. 55, Issue 27
  • DOI: 10.1002/anie.201510938

Direct Catalytic Anti-Markovnikov Hydroetherification of Alkenols
journal, November 2012

  • Hamilton, David S.; Nicewicz, David A.
  • Journal of the American Chemical Society, Vol. 134, Issue 45
  • DOI: 10.1021/ja309635w

RI-MP2: optimized auxiliary basis sets and demonstration of efficiency
journal, September 1998

Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization Reactions
journal, December 2015

  • Khomutnyk, Yaroslav Ya.; Argüelles, Alonso J.; Winschel, Grace A.
  • Journal of the American Chemical Society, Vol. 138, Issue 1
  • DOI: 10.1021/jacs.5b12528

Entrainer Effect on Photochirogenesis in Near- and Supercritical Carbon Dioxide: Dramatic Enhancement of Enantioselectivity
journal, June 2008

  • Nishiyama, Yasuhiro; Wada, Takehiko; Asaoka, Sadayuki
  • Journal of the American Chemical Society, Vol. 130, Issue 24
  • DOI: 10.1021/ja801254z

Iridium-Catalyzed, Intermolecular Hydroetherification of Unactivated Aliphatic Alkenes with Phenols
journal, June 2013

  • Sevov, Christo S.; Hartwig, John F.
  • Journal of the American Chemical Society, Vol. 135, Issue 25
  • DOI: 10.1021/ja4052153

Structure and Function of a Squalene Cyclase
journal, September 1997

A chiral ion-pair photoredox organocatalyst: enantioselective anti-Markovnikov hydroetherification of alkenols
journal, January 2017

  • Yang, Zhongbo; Li, Han; Li, Sujia
  • Organic Chemistry Frontiers, Vol. 4, Issue 6
  • DOI: 10.1039/C6QO00806B

Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols 1
journal, November 2006

  • Singh, Chandan; Pandey, Shilpi; Saxena, Gunjan
  • The Journal of Organic Chemistry, Vol. 71, Issue 24
  • DOI: 10.1021/jo061414z

Catalytic Markovnikov and anti-Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends
journal, June 2004

  • Beller, Matthias; Seayad, Jayasree; Tillack, Annegret
  • Angewandte Chemie International Edition, Vol. 43, Issue 26
  • DOI: 10.1002/anie.200300616

Tetrahydrofuran-Containing Macrolides: A Fascinating Gift from the Deep Sea
journal, March 2013

  • Lorente, Adriana; Lamariano-Merketegi, Janire; Albericio, Fernando
  • Chemical Reviews, Vol. 113, Issue 7
  • DOI: 10.1021/cr3004778

Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon
journal, February 2009

  • Clive, Derrick L. J.; Pham, Mai P.
  • The Journal of Organic Chemistry, Vol. 74, Issue 4
  • DOI: 10.1021/jo802629w

Simple, Chemoselective, Catalytic Olefin Isomerization
journal, November 2014

  • Crossley, Steven W. M.; Barabé, Francis; Shenvi, Ryan A.
  • Journal of the American Chemical Society, Vol. 136, Issue 48
  • DOI: 10.1021/ja5105602

Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter
journal, May 2015

  • Lin, Jin-Shun; Yu, Peng; Huang, Lin
  • Angewandte Chemie International Edition, Vol. 54, Issue 27
  • DOI: 10.1002/anie.201501762

Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model
journal, April 2003

  • Cossi, Maurizio; Rega, Nadia; Scalmani, Giovanni
  • Journal of Computational Chemistry, Vol. 24, Issue 6
  • DOI: 10.1002/jcc.10189

Ultrahigh-Resolution NMR Spectroscopy
journal, May 2014

  • Foroozandeh, Mohammadali; Adams, Ralph W.; Meharry, Nicola J.
  • Angewandte Chemie, Vol. 126, Issue 27
  • DOI: 10.1002/ange.201404111

Asymmetric Hydroalkoxylation of Non-Activated Alkenes: Titanium-Catalyzed Cycloisomerization of Allylphenols at High Temperatures
journal, February 2015

  • Schlüter, Johannes; Blazejak, Max; Boeck, Florian
  • Angewandte Chemie, Vol. 127, Issue 13
  • DOI: 10.1002/ange.201409252

Brønsted Acid Catalyzed Asymmetric S N 2-Type O-Alkylations
journal, February 2013

  • Čorić, Ilija; Kim, Ji Hye; Vlaar, Tjøstil
  • Angewandte Chemie, Vol. 125, Issue 12
  • DOI: 10.1002/ange.201209983

Extremely Active Organocatalysts Enable a Highly Enantioselective Addition of Allyltrimethylsilane to Aldehydes
journal, October 2016

  • Kaib, Philip S. J.; Schreyer, Lucas; Lee, Sunggi
  • Angewandte Chemie, Vol. 128, Issue 42
  • DOI: 10.1002/ange.201607828

Catalytic Markovnikov and anti-Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends
journal, September 2004

  • Beller, Matthias; Seayad, Jayasree; Tillack, Annegret
  • ChemInform, Vol. 35, Issue 39
  • DOI: 10.1002/chin.200439244

Rh-Catalyzed Enantioselective Hydrogenation of Vinyl Boronates for the Construction of Secondary Boronic Esters.
journal, October 2006

Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols.
journal, March 2007

Achiral Pyridine Ligand-Enabled Enantioselective Radical Oxytrifluoromethylation of Alkenes with Alcohols
journal, May 2017

  • Cheng, Yong-Feng; Dong, Xiao-Yang; Gu, Qiang-Shuai
  • Angewandte Chemie, Vol. 129, Issue 30
  • DOI: 10.1002/ange.201702925

A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis.
journal, December 2007

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
text, January 1988

  • Robert, Parr,; Chengteh, Lee,; Weitao, Yang,
  • The University of North Carolina at Chapel Hill University Libraries
  • DOI: 10.17615/zrp0-ry04
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    Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates
    journal, October 2018

    • Schreyer, Lucas; Kaib, Philip S. J.; Wakchaure, Vijay N.
    • Science, Vol. 362, Issue 6411
    • DOI: 10.1126/science.aau0817

    Multilayer 3D Chirality and Its Synthetic Assembly
    journal, June 2019

    Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation
    journal, August 2018

    • Xu, Chao; Muir, Calum W.; Leach, Andrew G.
    • Angewandte Chemie, Vol. 130, Issue 35
    • DOI: 10.1002/ange.201806956

    Chiral Brønsted Acid Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes and Asymmetric Hydroamination of Dienes
    journal, April 2019

    • Lin, Jin‐Shun; Li, Tao‐Tao; Jiao, Guan‐Yuan
    • Angewandte Chemie, Vol. 131, Issue 21
    • DOI: 10.1002/ange.201900955
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