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4 article(s) from Yamamoto, Yuki

Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

Yuki Yamamoto,
Yuki Konakazawa,
Kohsuke Fujiwara and
Akiya Ogawa

Beilstein J. Org. Chem. 2024, 20, 2577–2584, doi:10.3762/bjoc.20.216

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Scheme 1: (a) Conventional methods for the generation of Ar^• from Ar₃Bi, (b) our previous studies, and (c) th...

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Scheme 2: Scope for transition-metal-free synthesis of arylboronates 3 using triaylbismuthines 1 and diboron 2...

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Scheme 3: Control experiment of the metal-free borylation under an argon atmosphere.

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Figure 1: Comparison of the crude mixture of the reactions under (a) argon atmosphere or (b) open-air.

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Scheme 4: Radical-trapping experiments using TEMPO as a radical scavenger.

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Scheme 5: A proposed reaction pathway for the synthesis of arylboronates.

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Published 11 Oct 2024

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Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

Akiya Ogawa and
Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

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Figure 1: Resonance structures and reactivity of carbon monoxide.

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Figure 2: Resonance structures and reactivity of isocyanides.

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Scheme 1: Possible three pathways of the E• formation for imidoylation.

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Scheme 2: Radical addition of thiols to isocyanides.

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Scheme 3: Selective thioselenation and catalytic dithiolation of isocyanides.

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Scheme 4: Synthesis of carbacephem framework.

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Scheme 5: Sequential addition of (PhSe)₂ to ethyl propiolate and isocyanide.

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Scheme 6: Isocyanide insertion reaction into carbon-tellurium bonds.

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Scheme 7: Radical addition to isocyanides with disubstituted phosphines.

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Scheme 8: Radical addition to phenyl isocyanides with diphosphines.

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Scheme 9: Radical reaction of tin hydride and hydrosilane toward isocyanide.

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Scheme 10: Isocyanide insertion into boron compounds.

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Scheme 11: Isocyanide insertion into cyclic compounds containing boron units.

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Scheme 12: Photoinduced hydrodefunctionalization of isocyanides.

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Scheme 13: Tin hydride-mediated indole synthesis and cross-coupling.

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Scheme 14: 2-Thioethanol-mediated radical cyclization of alkenyl isocyanide.

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Scheme 15: Thiol-mediated radical cyclization of o-alkenylaryl isocyanide.

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Scheme 16: (PhTe)₂-assisted dithiolative cyclization of o-alkenylaryl isocyanide.

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Scheme 17: Trapping imidoyl radicals with heteroatom moieties.

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Scheme 18: Trapping imidoyl radicals with isocyano group.

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Scheme 19: Quinoline synthesis via aza-Bergman cyclization.

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Scheme 20: Phenanthridine synthesis via radical cyclization of 2-isocyanobiaryls.

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Scheme 21: Phenanthridine synthesis by radical reactions with AIBN, DBP and TTMSS.

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Scheme 22: Phenanthridine synthesis by oxidative cyclization of 2-isocyanobiaryls.

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Scheme 23: Phenanthridine synthesis using a photoredox system.

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Scheme 24: Phenanthridine synthesis induced by phosphorus-centered radicals.

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Scheme 25: Phenanthridine synthesis induced by sulfur-centered radicals.

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Scheme 26: Phenanthridine synthesis induced by boron-centered radicals.

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Scheme 27: Phenanthridine synthesis by oxidative cyclization of 2-aminobiaryls.

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Published 26 Aug 2024

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A two-phase bromination process using tetraalkylammonium hydroxide for the practical synthesis of α-bromolactones from lactones

Yuki Yamamoto,
Akihiro Tabuchi,
Kazumi Hosono,
Takanori Ochi,
Kento Yamazaki,
Shintaro Kodama,
Akihiro Nomoto and
Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 2906–2914, doi:10.3762/bjoc.17.198

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Scheme 1: General procedure for α-bromination of δ-valerolactone (1a) and the method described in this work.

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Scheme 2: Tetraalkylammonium salt-mediated intramolecular cyclization of 2a.

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Scheme 3: Synthesis of α-functionalized lactones using the two-phase system.

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Scheme 4: Synthesis of unsymmetrically functionalized sulfide 5 via the two-phase system-promoted intramolecu...

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Scheme 5: Sequential nucleophilic substitution in the two-phase system.

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Scheme 6: One-pot synthesis of 2-phenylthio-α-valerolactone 6.

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Published 09 Dec 2021

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Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

Dat Phuc Tran,
Yuki Sato,
Yuki Yamamoto,
Shin-ichi Kawaguchi,
Shintaro Kodama,
Akihiro Nomoto and
Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

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Scheme 1: Radical addition of Ph₂PPPh₂ and Ph₂P(X)PPh₂ to unsaturated C–C bonds.

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Scheme 2: The addition of Ph₂P(O)PPh₂ (1) to 1-octyne (2a).

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Scheme 3: Phosphinylphosphination of various terminal alkynes 2 with 1. ^aIsolated yields. V-40 = 1,1’-azobis(...

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Scheme 4: Attempted radical addition to internal alkynes and insight into the addition to 2n.

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Scheme 5: A plausible reaction pathway for the radical addition of Ph₂P(O)PPh₂ to terminal alkynes.

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Published 20 Apr 2021

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