1,2-aminochlorination;
oximes;
photoredox catalysis;
single electron transfer;
transfer reactions;
OLEFINS;
ACCESS;
D O I:
10.1021/acscatal.5c01290
中图分类号:
O64 [物理化学(理论化学)、化学物理学];
学科分类号:
070304 ;
081704 ;
摘要:
An efficient photoredox-catalyzed strategy for simultaneous C(sp3)-N and C(sp3)-Cl bond formation using bench-stable and easy-to-handle oxime-based transfer reagents is reported. The distinct reactivity of these surrogates allows for a regioselective and redox-neutral 1,2-aminochlorination of unactivated alkenes by a radical-polar crossover pathway, initiated by single-electron reduction of the surrogate and its subsequent fragmentation. This method expands the utility of oxime-based surrogates in alkene difunctionalization, offering a versatile and scalable platform for the direct synthesis of aminochlorinated products with broad functional group compatibility under mild conditions.
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068501, JapanHokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Yamaguchi, Yuto
Hirata, Yuki
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068501, JapanHokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Hirata, Yuki
Higashida, Kosuke
论文数: 0引用数: 0
h-index: 0
机构:
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068501, JapanHokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Higashida, Kosuke
Yoshino, Tatsuhiko
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, JapanHokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Yoshino, Tatsuhiko
Matsunaga, Shigeki
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068501, JapanHokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo 0600808, Japan
机构:
Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R ChinaHenan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
Chen, Xiaowei
Wei, Wenhui
论文数: 0引用数: 0
h-index: 0
机构:
Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R ChinaHenan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
Wei, Wenhui
Li, Chunyang
论文数: 0引用数: 0
h-index: 0
机构:
Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R ChinaHenan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
Li, Chunyang
Zhou, Hongwei
论文数: 0引用数: 0
h-index: 0
机构:
Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing, Zhejiang 314001, Peoples R ChinaHenan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
Zhou, Hongwei
Qiao, Baokun
论文数: 0引用数: 0
h-index: 0
机构:
Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R ChinaHenan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
Qiao, Baokun
Jiang, Zhiyong
论文数: 0引用数: 0
h-index: 0
机构:
Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R ChinaHenan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, JapanHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Yamaguchi, Yuto
Seino, Yusuke
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, JapanHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Seino, Yusuke
Suzuki, Akihiko
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, JapanHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Suzuki, Akihiko
Kamei, Yuji
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Ecole Polytech Fed Lausanne, EPFL, Inst Chem Sci & Engn, CH-1015 Lausanne, SwitzerlandHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Kamei, Yuji
Yoshino, Tatsuhiko
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Hokkaido Univ, Global Stn Biosurfaces & Drug Discovery, Sapporo, Hokkaido 0600812, JapanHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Yoshino, Tatsuhiko
Kojima, Masahiro
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, JapanHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Kojima, Masahiro
Matsunaga, Shigeki
论文数: 0引用数: 0
h-index: 0
机构:
Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
Hokkaido Univ, Global Stn Biosurfaces & Drug Discovery, Sapporo, Hokkaido 0600812, JapanHokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan