Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)-H Phosphorylation of Bicyclo[1.1.0]butanes

被引：0

作者：

Chen, Peng-Fei ^{[1
,2
]}

Dong, Meng-Yuan ^{[1
,2
]}

Han, Chun-Yu ^{[1
,2
]}

Li, Dong-Sheng ^{[1
,2
]}

Hong, Yang ^{[1
,2
]}

Xue, Fei ^{[3
]}

Liu, Fang ^{[1
,2
]}

Deng, Hong-Ping ^{[1
,2
]}

机构：

[1] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Peoples R China

[2] Nanjing Agr Univ, Coll Sci, Dept Chem, Nanjing 210095, Peoples R China

[3] Nanjing Forestry Univ, Inst Mat Phys & Chem, Coll Sci, Nanjing 210037, Peoples R China

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 03期

基金：

中国国家自然科学基金;

关键词：

STRAIN-RELEASE; CYCLOBUTANE; DERIVATIVES;

D O I：

10.1021/acs.orglett.4c04702

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp3)-H functionalization at the C2 position of BCBs remains scarce. Herein, a mild protocol for the hydrogen-evolution of C2 C(sp3)-H phosphorylation with BCBs enabled by photoinduced cobaloxime catalysis was realized in a regio- and diastereoselective manner. This oxidant- and additional photocatalyst-free method enabled C(sp3)-H phosphorylation with a wide range of BCBs and diarylphosphine oxides. The mechanism was studied via control experiments and DFT calculation. Moreover, the efficiency of this approach was highlighted in the synthesis of high-value, structurally complex molecules.

引用

页码：898 / 904

页数：7

共 50 条

[21] Direct regio- and stereoselective mono- and polyoxyfunctionalization of estrone derivatives at C(sp3)-H bonds
Ottenbacher, Roman V.
Samsonenko, Denis G.
Nefedov, Andrey A.
Bryliakov, Konstantin P.
Journal of Catalysis, 2022, 415 : 12 - 18
[22] Pd-Catalyzed Regio- and Stereoselective sp3 C-H Arylation of Primary Aliphatic Amines: Mechanistic Studies and Synthetic Applications
Ha, Hyeonbin
Choi, Ho Jeong
Park, Hahyoun
Gwon, Yunyeong
Lee, Jiin
Kwak, Jaesung
Kim, Min
Jung, Byunghyuck
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (07) : 1136 - 1145
[23] Cobalt(III)/Rhodium(III)-Catalyzed Regio- and Stereoselective Allylation of 8-methylquinoline via sp3 C-H Activation
Li, Na
Wang, Yahui
Kong, Lingheng
Chang, Junbiao
Li, Xingwei
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (16) : 3880 - 3885
[24] Photocatalytic regio- and stereoselective C(sp3)-H functionalization of benzylic and allylic hydrocarbons as well as unactivated alkanes
Li, Yanjun
Lei, Meng
Gong, Lei
NATURE CATALYSIS, 2019, 2 (11) : 1016 - 1026
[25] Photocatalytic regio- and stereoselective C(sp3)–H functionalization of benzylic and allylic hydrocarbons as well as unactivated alkanes
Yanjun Li
Meng Lei
Lei Gong
Nature Catalysis, 2019, 2 : 1016 - 1026
[26] Iron-Catalyzed Photoinduced Remote C(sp3)-H Amination of Free Alcohols
Xiong, Ni
Li, Yang
Zeng, Rong
ORGANIC LETTERS, 2021, 23 (22) : 8968 - 8972
[27] Gold-Catalyzed Regio- and Diastereoselective [3+2] Cycloaddition/Unactivated C(sp3)-H Bond Insertion of o-1,6-Enynyl Benzaldehydes to Oxa-Bridged Polycycles
Hu, Rui
Ji, Xiaowen
Zhang, Yongsheng
Chan, Philip Wai Hong
Rao, Weidong
ORGANIC LETTERS, 2025,
[28] Regio- and Stereoselective Pd-Catalyzed Direct Arylation of Unactivated sp3 C(3)-H Bonds of Tetrahydrofuran and 1,4-Benzodioxane Systems
Parella, Ramarao
Babu, Srinivasarao Arulananda
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (04): : 2339 - 2355
[29] Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp3)-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives
Fan, Zhoulong
Shu, Shiqi
Ni, Jiabin
Yao, Qizheng
Zhang, Ao
ACS CATALYSIS, 2016, 6 (02): : 769 - 774
[30] Photoinduced ligand-to-iron charge transfer enabled C(sp3)-H phosphorylation of hydrocarbons
Shi, Wei
Zhong, Ping-Fu
Qi, Xu-Kuan
Yang, Chao
Guo, Lin
Xia, Wujiong
GREEN CHEMISTRY, 2023, 25 (19) : 7817 - 7824

← 1 2 3 4 5 →