Photoredox Catalysis for Silyl-Mediated C-H Alkylation of Heterocycles with Non-Activated Alkyl Bromides

被引：23

作者：

Perkins, James J. ^{[1
]}

Schubert, Jeffrey W. ^{[1
]}

Streckfuss, Eric C. ^{[1
]}

Balsells, Jaume ^{[2
]}

ElMarrouni, Abdellatif ^{[1
]}

机构：

[1] Merck & Co Inc, MRL, Dept Discovery Chem, 770 Sumneytown Pike, West Point, PA 19486 USA

[2] Janssen Res & Dev LLC, Spring House, PA 19477 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 10期

关键词：

Alkylation; Minisci reaction; Photoredox catalysis; Synthetic methods; Visible light; LATE-STAGE FUNCTIONALIZATION; MEDICINAL CHEMISTS TOOLBOX; HETEROARENES; SUBSTITUTIONS; ALCOHOLS;

D O I：

10.1002/ejoc.201900611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of a Minisci reaction of electron-deficient heteroarenes with non-activated alkyl bromides under visible-light photoredox catalysis is disclosed. Optimization of the reaction led to identification of mild, general, and practical reaction conditions compatible with sensitive functional groups. The scope of this transformation allowed late-stage functionalization of pharmaceutical products containing electron-deficient heteroarenes in a parallel fashion.

引用

页码：1515 / 1522

页数：8

共 27 条

[11] Visible Light Photoredox Catalysis: Investigation of Distal sp3 C-H Functionalization of Tertiary Amines for Alkylation Reaction
Pandey, Ganesh
Jadhav, Deepak
Tiwari, Sandip Kumar
Singh, Bhawana
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2813 - 2818
[12] Design of catalysts for site-selective and enantioselective functionalization of non-activated primary C-H bonds
Liao, Kuangbiao
Yang, Yun-Fang
Lie, Yingzi
Sanders, Jacob N.
Houk, K. N.
Musaev, Djamaladdin G.
Davies, Huw M. L.
NATURE CHEMISTRY, 2018, 10 (10) : 1048 - 1055
[13] Photoredox-Mediated Minisci C-H Alkylation Reactions between N-Heteroarenes and Alkyl Iodides with Peroxyacetate as a Radical Relay Initiator
Wang, Zhen
Dong, Jianyang
Hao, Yanan
Li, Yongqiang
Liu, Yuxiu
Song, Hongjian
Wang, Qingmin
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24): : 16245 - 16253
[14] Photoredox-HAT Catalysis for Primary Amine α-C-H Alkylation: Mechanistic Insight with Transient Absorption Spectroscopy
Sneha, Mahima
Thornton, Georgia L.
Lewis-Borrell, Luke
Ryder, Alison S. H.
Espley, Samuel G.
Clark, Ian P.
Cresswell, Alexander J.
Grayson, Matthew N.
Orr-Ewing, Andrew J.
ACS CATALYSIS, 2023, 13 (12) : 8004 - 8013
[15] C(2)H-Alkylation of (Benz)oxazoles with Tertiary Alkyl Chlorides and Bromides under Photoinduced Palladium Catalysis
Lavrentev, I. V.
Astakhov, A. V.
Shepelenko, K. E.
Chernyshev, V. M.
DOKLADY CHEMISTRY, 2023, 513 (01) : 327 - 336
[16] Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides
Zhou, Wen-Jun
Cao, Guang-Mei
Shen, Guo
Zhu, Xing-Yong
Gui, Yong-Yuan
Ye, Jian-Heng
Sun, Liang
Liao, Li-Li
Li, Jing
Yu, Da-Gang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15683 - 15687
[17] DNA-encoded C-H functionality via photoredox-mediated hydrogen atom transformation catalysis
Shan, Jinming
Ling, Xing
Liu, JiaXiang
Wang, Xuan
Lu, Xiaojie
BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 42
[18] C(sp3)-C(sp3) Cross-Coupling of Alkyl Bromides and Ethers Mediated by Metal and Visible Light Photoredox Catalysis
Santos, Marilia S.
Correa, Arlene G.
Paixao, Marcio W.
Koenig, Burkhard
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (12) : 2367 - 2372
[19] Hydroxy Functionalization of Non-Activated C-H and C=C Bonds: New Perspectives for the Synthesis of Alcohols through Biocatalytic Processes
Groeger, Harald
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (12) : 3067 - 3069
[20] Aluminum-Mediated C6-Selective C-H Alkylation of 2-Carbamoylbenzofuran by Nickel Catalysis
Okumura, Shogo
Nakao, Yoshiaki
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1355 - 1357

← 1 2 3 →