Publications
Publications
[112] Harnessing the reactivity of captodative radicals: photocatalytic α-pyridination of glycyl derivatives through reversible radical coupling
Ken Yamazaki, Shuta Akimoto, Tomoya Miura
Org. Biomol. Chem. 2025, 23, xxxx-xxxx. DOI: 10.1039/D5OB00675A
From the themed collection: New Talent
[111] 1,2-Acylcyanation of Styrenes by Photoinduced Nickel Catalysis to Generate Acyl Radicals from Acyl Fluorides
Naoki Oku, Reo Saeki, Yuriko Doi, Ken Yamazaki, Tomoya Miura
Org. Lett. 2025, 27, 3361-3367. DOI: 10.1021/acs.orglett.5c00761
Highlighted in Synfacts 2025, 21, 699.
[110] Efficient Nickel Precatalysts for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions
Morgan E. John, Michael J. Nutt, Josephine E. Offer, Jeremy A. Duczynski, Ken Yamazaki, Tomoya Miura, Stephen A. Moggach, George A. Koutsantonis, Reto Dorta, Scott G. Stewart
Angew. Chem. Int. Ed. 2025, 64, e202504108. DOI: 10.1002/anie.202504108
Selected as a Hot Paper!
[109] Stereoselective Preparation and Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkenyl Sulfoximines
Kosuke Yasui, Yuichiro Tomishima, Tomoya Miura, Ken Yamazaki, and Koji Hirano
Angew. Chem. Int. Ed. 2025, 64, e202420949. DOI: 10.1002/anie.202420949
Selected as a Very Important Paper!
[108] Synthesis of α-Boryl-α-Substituted Allylboronates from Propyne
Hiro Takayanagi, Naoki Oku, Ken Yamazaki, and Tomoya Miura
Org. Lett. 2024, 26, 10108-10113. DOI: 10.1021/acs.orglett.4c03683
[107] A DFT Mechanistic Study on the Aza-Aldol Reaction of Boron Aza-
Enolates: Relative Stability of Six-Membered Transition State and Its
Relevance to the Coordination Mode of the Leaving Group
Sho Miyakawa, Ray Miyazaki, Tomoya Miura, and Jun-ya Hasegawa
J. Org. Chem. 2024, 89, 13913-13922. DOI: 10.1021/acs.joc.4c00957
[106] Visible-Light-Driven 1,2-Hydro(cyanomethylation) of Alkenes with Chloroacetonitrile
[105] Ligand-Controlled Regiodivergence in Nickel-Catalyzed Vinylcyclopropane Rearrangement
Keiichi Irifune, Ken Yamazaki, Takayuki Nakamuro, Masahiro Murakami, and Tomoya Miura
Angew. Chem. Int. Ed. 2023, 62, e202307826. DOI: 10.1002/anie.202307826
[104] Cu-Catalyzed Double C(sp3)-H Functionalization of Ethylarenes to Form Arylethanolamines
[103] Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids
Naoki Oku, Masahiro Murakami, and Tomoya Miura
Org. Lett. 2022, 24, 1616-1619. DOI: 10.1021/acs.orglett.2c00121
Selected as a Supplementary Cover!
[102] Synthesis, Structure, and Dynamics of Chiral Eight-Membered Cyclic Molecules with Thienylene and Cyclopropylene Units Alternately Connected
Tomoya Miura, Yumi Ishihara, Takayuki Nakamuro, Shunsuke Moritani, Yuuya Nagata, and Masahiro Murakami
Chem. Eur. J. 2022, 28, e202103962. DOI: 10.1002/chem.202103962
Highlighted in Synfacts, 2022, 18, 0267.
[101] 1,2-Acyl Migration with α-Imino Rhodium Carbenoids Leading to Substituted 1-Naphthols
Tomoya Miura, Shunsuke Moritani, Yota Shiratori, and Masahiro Murakami
Chem. Commun. 2022, 58, 2710-2713. DOI: 10.1039/D1CC06349A
[100] Stereo- and Enantioselective Synthesis of Propionate-Derived Trisubstituted Alkene Motifs
Tomoya Miura, Naoki Oku, Yota Shiratori, Yuuya Nagata, and Masahiro Murakami
Chem. Eur. J. 2021, 27, 3861-3868. DOI: 10.1002/chem.202004930
Selected as a Hot Paper !
[99] Regioselective 1,3-Dipolar Cycloaddition of Nitriles with Nitrile Imines Generated from Tetrazoles
Tomoya Miura, Kohei Hagiwara, Takayuki Nakamuro, Yuuya Nagata, Naoki Oku, and Masahiro Murakami
Chem. Lett. 2021, 50, 131-135. DOI: 10.1246/cl.200634
[98] Synthesis of Alkyl Sulfones from Alkenes and Tosylmethylphosphonium Iodide through Photo-Promoted C-C Bond Formation
Tomoya Miura, Daisuke Moriyama, Sho Miyakawa, and Masahiro Murakami
Chem. Lett. 2020, 49, 1382-1385. DOI: 10.1246/cl.200530
[97] Chiral Macrocycles Having C3 Symmetry Resulting from Orientation of Thiophene Rings
Tomoya Miura, Takayuki Nakamuro, Yumi Ishihara, Yuuya Nagata and Masahiro Murakami
Angew. Chem. Int. Ed. 2020, 59, 20475-20479. DOI: 10.1002/anie.202009781
Selected as a Hot Paper !
[96] A One-Pot Reaction of α-Imino Rhodium Carbenoids and Halohydrins: Access to 2,6-Substituted Dihydro-2H-1,4-oxazines
Kieran D. Jones, Michael J. Nutt, Elena Comninos, Alexandre N. Sobolev, Stephen A. Moggach, Tomoya Miura, Masahiro Murakami, and Scott G. Stewart
Org. Lett. 2020, 22, 3490-3494. DOI: 10.1021/acs.orglett.0c00947
[95] Asymmetric Synthesis and Stereochemical Assignment of 12C/13C Isotopomers
Tomoya Miura, Takayuki Nakamuro, Yuuya Nagata, Daisuke Moriyama, Scott G. Stewart, and Masahiro Murakami
J. Am. Chem. Soc. 2019, 141, 13341-13345. DOI: 10.1021/jacs.9b07181
[94] Diastereo- and Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols in Two Steps from Terminal Alkynes
Tomoya Miura, Naoki Oku, and Masahiro Murakami
Angew. Chem. Int. Ed. 2019, 58, 14620-14624. DOI: 10.1002/anie.201908299
[93] Generation of Boron Aza-Enolates by a Nickel-Catalyzed Reaction of Triazoles with Pinacolborane and Their Addition to Aldehydes
Tomoya Miura, Sho Miyakawa, Takayuki Nakamuro, and Masahiro Murakami
Chem. Lett. 2019, 48, 965-967. DOI: 10.1246/cl.190290
[92] Cyclization Reaction of 4-Acyl-1,2,3-triazoles Possessing Phenyl Rings through Generation of Electron-Deficient Carbenoids
Qiang Zhao, Tomoya Miura, and Masahiro Murakami
Chem. Lett. 2019, 48, 510-512. DOI: 10.1246/cl.190074
[91] Photoinduced 1,2-Hydro(cyanomethylation) of Alkenes with a Cyanomethylphosphonium Ylide
Tomoya Miura, Daisuke Moriyama, Yuuta Funakoshi, and Masahiro Murakami
Synlett 2019, 30, 511-514. DOI: 10.1055/s-0037-1612230
Published as part of 30 Years SYNLETT – Pearl Anniversary Issue
[90] Synthesis of γ-Boryl-Substituted Homoallylic Alcohols with Anti Stereochemistry Based on a Double-Bond Transposition Protocol
Tomoya Miura, Junki Nakahashi, Takanori Sasatsu, and Masahiro Murakami
Angew. Chem. Int. Ed. 2019, 58, 1138-1142. DOI: 10.1002/anie.201811205
[89] Light/Copper Relay for Aerobic Fragmentation of Lignin Model Compounds
Wang Zhou, Junki Nakahashi, Tomoya Miura, and Masahiro Murakami
Asian J. Org. Chem. 2018, 7, 2431-2434. DOI: 10.1002/ajoc.201800520
[88] Synthesis of Elongated Esters from Alkenes
Tomoya Miura, Yuuta Funakoshi, Junki Nakahashi, Daisuke Moriyama, and Masahiro Murakami
Angew. Chem. Int. Ed. 2018, 57, 15455-15459. DOI: 10.1002/anie.201809115
[87] Enantioselective Denitrogenative Annulation of 1H-Tetrazoles with Styrenes Catalyzed by Rhodium
Takayuki Nakamuro, Kohei Hagiwara, Tomoya Miura, and Masahiro Murakami
Angew. Chem. Int. Ed. 2018, 57, 5497-5500. DOI: 10.1002/anie.201801283
[86] Photo-Catalyzed Ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage
Wang Zhou, Tomoya Miura, and Masahiro Murakami
Angew. Chem. Int. Ed. 2018, 57, 5139-5142. DOI: 10.1002/anie.201801305
[85] Selective Functionalization of Aromatic C(sp2 )–H Bonds in the Presence of Benzylic C(sp3)–H Bonds by Electron-Deficient Carbenoid Generated from 4-Acyl-1-sulfonyl-1,2,3-triazoles
Tomoya Miura, Qiang Zhao, Masahiro Murakami
Angew. Chem. Int. Ed. 2017, 56, 16645-16649. DOI: 10.1002/anie.201709384
[84] Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts
Tomoya Miura, Junki Nakahashi, Wang Zhou, Yota Shiratori, Scott G. Stewart, and Masahiro Murakami
J. Am. Chem. Soc. 2017, 139, 10903-10908. DOI: 10.1021/jacs.7b06408
[83] Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid
Tomoya Miura, Junki Nakahashi, and Masahiro Murakami
Angew. Chem. Int. Ed. 2017, 56, 6989-6993. DOI: 10.1002/anie.201702611
[82] Synthesis of Enantiopure C3-Symmetric Triangular Molecules
Tomoya Miura, Takayuki Nakamuro, Scott G. Stewart, Yuuya Nagata, and Masahiro Murakami
Angew. Chem. Int. Ed. 2017, 56, 3334-3338. DOI: 10.1002/anie.201612585
[81] Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-Alkenols
Tomoya Miura, Takamasa Tanaka, Qiang Zhao, Scott G. Stewart, and Masahiro Murakami
Helv. Chim. Acta. 2017, 100, e1600320. DOI: 10.1002/hlca.201600320
[80] Synthesis of Penta-2,4-dien-1-imines and 1,2-Dihydropyridines by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-(Siloxy)furans
Yuuta Funakoshi, Tomoya Miura, and Masahiro Murakami
Org. Lett. 2016, 18, 6284-6287. DOI: 10.1021/acs.orglett.6b03143
[79] Asymmetric Synthesis of Cyclopropylmethanamines by Rhodium-Catalyzed Cyclopropanation of Pinacol Allylboronate with N-Sulfonyl-1,2,3-triazoles
Tomoya Miura, Takayuki Nakamuro, Hiroki Nikishima, and Masahiro Murakami
Chem. Lett. 2016, 45, 1003-1005. DOI: 10.1246/cl.160465
Selected as an Editor's Choice !
[78] A syn-Selective Aza-Aldol Reaction of Boron Aza-Enolates Generated from N-Sulfonyl-1,2,3-Triazoles and 9-BBN-H
Tomoya Miura, Takayuki Nakamuro, Sho Miyakawa, and Masahiro Murakami
Angew. Chem. Int. Ed. 2016, 55, 8732-8735. DOI: 10.1002/anie.201603270
[77] Rhodium-Catalyzed Dehydrogenative Borylation of Aliphatic Terminal Alkenes with Pinacolborane
Masao Morimoto, Tomoya Miura, and Masahiro Murakami
Angew. Chem. Int. Ed. 2015, 54, 12659-12663. DOI: 10.1002/anie.201506328
[76] Site-Selective Introduction of an Enamido Group at the C(3)-Position of Indoles
Tomoya Miura, Qiang Zhao, Yuuta Funakoshi, and Masahiro Murakami
Heterocycles 2015, 91, 1579-1584. DOI: 10.3987/COM-15-13261
[75] A Reaction of Triazoles with Thioesters Producing β-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Linkage
Tomoya Miura, Yoshikazu Fujimoto, Yuuta Funakoshi, and Masahiro Murakami
Angew. Chem. Int. Ed. 2015, 54, 9967-9970. DOI: 10.1002/anie.201504013
[74] Thermal Reaction of 4-(p-Aminophenyl)-1-sulfonyl-1,2,3-triazoles Furnishing Benzoyl Cyanides Through N-Sulfinyl Imine Intermediates
Tomoya Miura, Qiang Zhao, Yuuta Funakoshi, and Masahiro Murakami
Chem. Lett. 2015, 44, 967-969. DOI: 10.1246/cl.150320
[73] Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
Tomoya Miura, Yuuta Funakoshi, Yoshikazu Fujimoto, Junki Nakahashi, and Masahiro Murakami
Org. Lett. 2015, 17, 2454-2457. DOI: 10.1021/acs.orglett.5b00960
[72] Synthesis of α,β,γ,δ-Unsaturated Imines from N-Sulfonyl-1,2,3-triazoles and Allenes through Rhodium-Catalyzed Cyclopropanation and Thermal Rearrangement
Tomoya Miura, Takayuki Nakamuro, Tsuneaki Biyajima, and Masahiro Murakami
Chem. Lett. 2015, 44, 700-702. DOI: 10.1246/cl.150080
[71] Synthesis of trans-Cycloalkenes via Enantioselective Cyclopropanation and Skeletal Rearrangement
Tomoya Miura, Takayuki Nakamuro, Chia-Jung Liang, and Masahiro Murakami
J. Am. Chem. Soc. 2014, 136, 15905-15908. DOI: 10.1021/ja5096045
[70] Direct Synthesis of 2,5-Dihydropyrroles from Terminal Alkynes, Azides, and Propargylic Alcohols by Relay Actions of Copper, Rhodium, and Gold
Tomoya Miura, Takamasa Tanaka, Kohei Matsumoto, and Masahiro Murakami
Chem. Eur. J. 2014, 49, 16078-16082. DOI: 10.1002/chem.201405357
[69] The stereoselective synthesis of α-amino aldols starting from terminal alkynes
Tomoya Miura, Takayuki Nakamuro, Kentaro Hiraga and Masahiro Murakami
Chem. Commun. 2014, 50, 10474-10477. DOI: 10.1039/C4CC04786A
[68] Direct Production of Enaminones from Terminal Alkynes via Rhodium-Catalyzed Reaction of Formamides with N-Sulfonyl-1,2,3-triazoles
Tomoya Miura, Yuuta Funakoshi, Takamasa Tanaka, and Masahiro Murakami
Org. Lett. 2014, 16, 2760-2763. DOI: 10.1021/ol5010774
[67] Construction of Homoallylic Alcohols from Terminal Alkynes and Aldehydes with Installation of syn-Stereochemistry
Tomoya Miura, Yui Nishida, and Masahiro Murakami
J. Am. Chem. Soc. 2014, 136, 6223-6226. DOI: 10.1021/ja502169d
[66] Intramolecular Dearomatizing [3+2] Annulation of α-Imino Carbenoids with Aryl Rings Furnishing 3,4-Fused Indole Skeletons
Tomoya Miura, Yuuta Funakoshi, and Masahiro Murakami
J. Am. Chem. Soc. 2014, 136, 2272-2275. DOI: 10.1021/ja412663a
Highlighted in Synfacts, 2014, 10, 849 !
Highlighted in Organic Chemistry Portal !
Ranked as a top 1% cited paper according to Thomson Reuters !
[65] Doyle-Kirmse Reaction Using Triazoles Leading to One-pot Multi-functionalization of Terminal Alkynes
Tomoya Miura, Takamasa Tanaka, Akira Yada, and Masahiro Murakami
Chem. Lett. 2013, 42, 1308-1310. DOI: 10.1246/cl.130521
Selected as an Editor's Choice !
[64] Stereoselective Synthesis of 2,3-Dihydropyrroles from Terminal Alkynes, Azides, and α,β-Unsaturated Aldehydes via N-Sulfonyl-1,2,3-triazoles
Tomoya Miura, Takamasa Tanaka, Kentaro Hiraga, Scott G. Stewart, and Masahiro Murakami
J. Am Chem. Soc. 2013, 135, 13652-13655. DOI: 10.1021/ja407166r
[63] Enantioselective Synthesis of anti-Homoallylic Alcohols from Terminal Alkynes and Aldehydes Based on Concomitant Use of a Cationic Iridium Complex/a Chiral Phosphoric Acid
Tomoya Miura, Yui Nishida, Masao Morimoto, and Masahiro Murakami
J. Am Chem. Soc. 2013, 135, 11497-11500. DOI: 10.1021/ja405790t
[62] Regiocontrolled Synthesis of Polysubstituted Pyrroles Starting from Terminal Alkynes, Sulfonyl Azides, and Allenes
Tomoya Miura, Kentaro Hiraga, Tsuneaki Biyajima, Takayuki Nakamuro, and Masahiro Murakami
Org. Lett. 2013, 15, 3298-3301. DOI: 10.1021/ol401340u
[61] Nickel-Catalyzed [2+2+2] Cycloaddition Reaction of Isocyanates with 1,3-Dienes
Masao Morimoto, Yui Nishida, Tomoya Miura, and Masahiro Murakami
Chem. Lett. 2013, 42, 550-552. DOI: 10.1246/cl.130082
[60] One-Pot Procedure for the Introduction of Three Different Bonds onto Terminal Alkynes through N-Sulfonyl-1,2,3-Triazole Intermediates
Tomoya Miura, Takamasa Tanaka, Tsuneaki Biyajima, Akira Yada, and Masahiro Murakami
Angew. Chem. Int. Ed. 2013, 52, 3883-3886. DOI: 10.1002/anie.201209603
[59] Synthesis of Enaminones by Rhodium-Catalyzed Denitrogenative Rearrangement of 1-(N-Sulfonyl-1,2,3-triazol-4-yl)alkanols
Tomoya Miura, Yuuta Funakoshi, Masao Morimoto, Tsuneaki Biyajima, and Masahiro Murakami
J. Am. Chem. Soc. 2012, 134, 17440-17443. DOI: 10.1021/ja308285r
[58] Copper-Catalyzed Amination of Silyl Ketene Acetals with N-Chloroamines
Tomoya Miura, Masao Morimoto, and Masahiro Murakami
Org. Lett. 2012, 14, 5214-5217. DOI: 10.1021/ol302331k
[57] Synthesis of (1H)-Isochromen-1-imines by Nickel-catalyzed Reaction of 2-Iodobenzamides with Alkynes
Tomoya Miura, Kentaro Hiraga, Takeharu Toyoshima, Motoshi Yamauchi, and Masahiro Murakami
Chem. Lett. 2012, 41, 798-800. DOI: 10.1246/cl.2012.798
Selected as "New Synthetic Methods" in J. Synth. Org. Chem. Jpn. 2013, 71, 74 !
[56] Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles
Tomoya Miura, Tsuneaki Biyajima, Tetsuji Fujii, and Masahiro Murakami
J. Am. Chem. Soc. 2012, 134, 194-196. DOI: 10.1021/ja2104203
[55] Rhodium-Catalyzed Reaction of 1-Alkenylboronates with Aldehydes Leading to Allylation Products
Hiroshi Shimizu, Tomohiro Igarashi, Tomoya Miura, and Masahiro Murakami
Angew. Chem. Int. Ed. 2011, 50, 11465-11469. DOI: 10.1002/anie.201105148
[54] Selective 1:2 Coupling of Aldehydes and Allenes with Control of Regiochemistry
Takeharu Toyoshima, Tomoya Miura, and Masahiro Murakami
Angew. Chem. Int. Ed. 2011, 50, 10436-10439. DOI: 10.1002/anie.201105077
[53] Nickel-Catalyzed Synthesis of 1,3,5-Trisubstituted Hydantoins from Acrylates and Isocyanates
Tomoya Miura, Yusuke Mikano, and Masahiro Murakami
Org. Lett. 2011, 13, 3560-3563. DOI: 10.1021/ol200957y
[52] Synthesis of Cross-Conjugated Trienes by Rhodium-Catalyzed Dimerization Reaction of Monosubstituted Allenes
Tomoya Miura, Tsuneaki Biyajima, Takeharu Toyoshima, and Masahiro Murakami
Beilstein. J. Org. Chem. 2011, 7, 578-581. DOI: 10.3762/bjoc.7.67
[51] Palladium-Catalyzed Denitrogenation Reaction of 1,2,3-Benzotriazin-4(3H)-ones Incorporating Isocyanides
Tomoya Miura, Yui Nishida, Masao Morimoto, Motoshi Yamauchi, and Masahiro Murakami
Org. Lett. 2011, 13, 1429-1431. DOI: 10.1021/ol103143a
[50] Stereoselective Synthesis of 3-(1-Cyanoalkylidene)oxindoles by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Copper(I) Cyanide
Tomoya Miura, Takeharu Toyoshima, Osamu Kozawa, and Masahiro Murakami
Chem. Lett. 2010, 39, 1132-1133. DOI: 10.1246/cl.2010.1132
Selected as an Editor's Choice !
[49] Synthesis of 3,3-Disubstituted Oxindoles by Palladium-Catalyzed Tandem Reaction of 2-(Alkynyl)aryl Isocyanates with Benzylic Alcohols
Takeharu Toyoshima, Yusuke Mikano, Tomoya Miura, and Masahiro Murakami
Org. Lett. 2010, 12, 4584-4587. DOI: 10.1021/ol101892b
[48] Palladium-Catalyzed Allylation Reaction of Alkynylborates
Naoki Ishida, Tatsuo Shinmoto, Shota Sawano, Tomoya Miura, and Masahiro Murakami
Bull. Chem. Soc. Jpn. 2010, 83, 1380-1385. DOI: 10.1246/bcsj.20100189
Selected as "New Synthetic Methods" in J. Synth. Org. Chem. Jpn. 2011, 69, 623 !
[47] Enantioselective [2+2+2] Cycloaddition Reaction of Isocyanates and Allenes Catalyzed by Nickel
Tomoya Miura, Masao Morimoto, and Masahiro Murakami
J. Am. Chem. Soc. 2010, 132, 15836-15838. DOI: 10.1021/ja105541r
Highlighted in Synfacts, 2011, 18 !
Selected as a front cover of J. Am. Chem. Soc. 2010, issue 45 !
Development of Catalytic Reactions Using N-Sulfonyl-1,2,3-triazoles as Precursors of Carbene Complexes
Development of Terminal Alkynes in Highly Efficient Molecular Conversion Reactions
Tomoya Miura
Kagaku to Kogyo. 2014, 67, 998-999.