Intermolecular Conjugate Addition of Pyrroloindoline and Furoindoline Radicals to α,β-Unsaturated Enones via Photoredox Catalysis

被引：25

作者：

Zhou, Shupeng ^{[1
]}

Zhang, Deliang ^{[1
]}

Sun, Yu ^{[1
]}

Li, Ruofan ^{[1
]}

Zhang, Wenhao ^{[1
]}

Li, Ang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 13期

基金：

中国国家自然科学基金;

关键词：

alkaloid-terpenoid hybrids; conjugate addition; furoindolines; photoredox catalysis; pyrroloindolines; VISIBLE-LIGHT PHOTOCATALYSIS; C-H BONDS; SYNTHETIC APPLICATIONS; MERGING PHOTOREDOX; CHAIN REACTIONS; CYCLIZATIONS; GENERATION; REACTIVITY; CHEMISTRY; DESIGN;

D O I：

10.1002/adsc.201400702

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We have developed an intermolecular conjugate addition of 3a-pyrroloindoline/furoindoline radicals to alpha,beta-unsaturated enones, through visible-light photoredox catalysis. Ir(ppy)(2)(dtbbpy) PF6 was found to be an effective promoter to initiate this reaction from readily available 3a-bromopyrroloindolines/furoindolines. This method was exploited to prepare a series of indole terpenoid-like compounds of potential biological interest.

引用

页码：2867 / 2872

页数：6

共 50 条

[1] Intermolecular Reactions of Pyridyl Radicals with Olefins via Photoredox Catalysis
Seath, Ciaran P.
Jui, Nathan T.
SYNLETT, 2019, 30 (14) : 1607 - 1614
[2] Enantioselective Conjugate Additions of α-Amino Radicals via Cooperative Photoredox and Lewis Acid Catalysis
Espelt, Laura Ruiz
McPherson, Iain S.
Wiensch, Eric M.
Yoon, Tehshik P.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) : 2452 - 2455
[3] Radical conjugate addition of alkyl bromides to α,β-unsaturated amides and esters by visible-light photoredox catalysis
El Marrouni, Abdellatif
Balsells, Jaume
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[4] Intermolecular conjugate addition of alkyl radicals on solid phase
Zhu, XW
Ganesan, A
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (02): : 157 - 162
[5] Highly enantioselective organocatalytic conjugate addition of malonates to acyclic α,β-unsaturated enones
Halland, N
Aburel, PS
Jorgensen, KA
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (06) : 661 - 665
[6] Generation and Alkylation of α-Carbamyl Radicals via Organic Photoredox Catalysis
McManus, Joshua B.
Onuska, Nicholas P. R.
Nicewicz, David A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (29) : 9056 - 9060
[7] Enantioselective Synthesis of Functionalized Nitrocyclopropanes by Organocatalytic Conjugate Addition of Bromonitroalkanes to α,β-Unsaturated Enones
Lv, Jian
Zhang, Jiaming
Lin, Zhu
Wang, Yongmei
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (04) : 972 - 979
[8] Asymmetric conjugate addition of alkynylboronates to enones: Rationale for the intriguing catalysis exerted by binaphthols
Pellegrinet, SC
Goodman, JM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) : 3116 - 3117
[9] Asymmetric conjugate addition of alkynylboronates to enones: Rationale for the intriguing catalysis exerted by binaphthols
Pellegrinet, Silvina C.
Goodman, Jonathan M.
Journal of the American Chemical Society, 2006, 128 (10): : 3116 - 3117
[10] Intermolecular Regioselective Alkylarylation of Vinylarenes via Photoredox/Nickel Dual Catalysis
Pan, Xian-Hua
Hou, Ya-Ping
Shi, Chang-Xin
Wang, Ya-Ping
Niu, Rui-Qi
Guo, Lei
ORGANIC LETTERS, 2024, 26 (35) : 7291 - 7296

← 1 2 3 4 5 →