Room-Temperature Ligation of Iminophosphoranes with gem-Difluoroalkenes

Masaru Tanioka; Fuudai Enomoto; Fumino Kitamura; Ryunosuke Nakamura; Akinari Takano; Shohei Kanayama; Aki Koyama; Tsuyoshi Yamada; Yuji Matsuya

doi:10.1021/acs.joc.4c02874

Room-Temperature Ligation of Iminophosphoranes with gem-Difluoroalkenes

Masaru Tanioka^*, Fuudai Enomoto, Fumino Kitamura, Ryunosuke Nakamura, Akinari Takano, Shohei Kanayama, Aki Koyama, Tsuyoshi Yamada, Yuji Matsuya^*

^*この論文の責任著者

薬品製造学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

抄録

Ligation reactions that proceed at room temperature under aqueous conditions and without catalysts are in high demand, including bioorthogonal reactions. We report a mild amide-ligation reaction of iminophosphoranes with gem-difluoroalkenes. Through experimental and theoretical analyses of intermolecular and intramolecular amidation reactions, we found that the Staudinger-Bertozzi ligation-type reaction of iminophosphoranes with gem-difluoroalkenes is an excellent reaction that proceeds rapidly at room temperature in an aqueous solvent.

本文言語	英語
ジャーナル	Journal of Organic Chemistry
DOI	https://doi.org/10.1021/acs.joc.4c02874
出版ステータス	受理済み/印刷中 - 2025

ASJC Scopus 主題領域

有機化学

文献へのアクセス

10.1021/acs.joc.4c02874

引用スタイル

@article{252a5943f0ed455abbc54da825bd7e1b,

title = "Room-Temperature Ligation of Iminophosphoranes with gem-Difluoroalkenes",

abstract = "Ligation reactions that proceed at room temperature under aqueous conditions and without catalysts are in high demand, including bioorthogonal reactions. We report a mild amide-ligation reaction of iminophosphoranes with gem-difluoroalkenes. Through experimental and theoretical analyses of intermolecular and intramolecular amidation reactions, we found that the Staudinger-Bertozzi ligation-type reaction of iminophosphoranes with gem-difluoroalkenes is an excellent reaction that proceeds rapidly at room temperature in an aqueous solvent.",

author = "Masaru Tanioka and Fuudai Enomoto and Fumino Kitamura and Ryunosuke Nakamura and Akinari Takano and Shohei Kanayama and Aki Koyama and Tsuyoshi Yamada and Yuji Matsuya",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.joc.4c02874",

language = "英語",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Room-Temperature Ligation of Iminophosphoranes with gem-Difluoroalkenes

AU - Tanioka, Masaru

AU - Enomoto, Fuudai

AU - Kitamura, Fumino

AU - Nakamura, Ryunosuke

AU - Takano, Akinari

AU - Kanayama, Shohei

AU - Koyama, Aki

AU - Yamada, Tsuyoshi

AU - Matsuya, Yuji

PY - 2025

Y1 - 2025

N2 - Ligation reactions that proceed at room temperature under aqueous conditions and without catalysts are in high demand, including bioorthogonal reactions. We report a mild amide-ligation reaction of iminophosphoranes with gem-difluoroalkenes. Through experimental and theoretical analyses of intermolecular and intramolecular amidation reactions, we found that the Staudinger-Bertozzi ligation-type reaction of iminophosphoranes with gem-difluoroalkenes is an excellent reaction that proceeds rapidly at room temperature in an aqueous solvent.

AB - Ligation reactions that proceed at room temperature under aqueous conditions and without catalysts are in high demand, including bioorthogonal reactions. We report a mild amide-ligation reaction of iminophosphoranes with gem-difluoroalkenes. Through experimental and theoretical analyses of intermolecular and intramolecular amidation reactions, we found that the Staudinger-Bertozzi ligation-type reaction of iminophosphoranes with gem-difluoroalkenes is an excellent reaction that proceeds rapidly at room temperature in an aqueous solvent.

UR - http://www.scopus.com/inward/record.url?scp=85219339007&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.4c02874

DO - 10.1021/acs.joc.4c02874

M3 - 学術論文

AN - SCOPUS:85219339007

SN - 0022-3263

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

Room-Temperature Ligation of Iminophosphoranes with gem-Difluoroalkenes

抄録

ASJC Scopus 主題領域

文献へのアクセス

フィンガープリント

引用スタイル