Aryldiazonium Salt-Triggered [2+2+1] Heteroannulation of Indoles by an Arylhydrazone Radical-Relayed 1,5-Hydrogen Atom Transfer

被引：4

作者：

Ouyang, Jun-Yao ^{[1
]}

Shen, Fang-Fang ^{[1
]}

Zhao, Han-Qing ^{[1
]}

Chen, Jia-Jie ^{[1
]}

Wen, Zhu-Dong ^{[1
]}

Jiang, Hui-Min ^{[1
]}

Qin, Jing-Hao ^{[1
]}

Sun, Qing ^{[1
]}

Li, Jin-Heng ^{[2
,3
,4
]}

Ouyang, Xuan-Hui ^{[1
]}

机构：

[1] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Control, Nanchang 330063, Peoples R China

[2] Qingdao Univ Sci, Coll Chem, State Key Lab Base Ecochem Engn, Qingdao 266042, Peoples R China

[3] Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

[4] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 35期

关键词：

C-H FUNCTIONALIZATION; LIGHT; DERIVATIVES; GENERATION;

D O I：

10.1021/acs.orglett.3c02373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented three-component [2 + 2 + 1] annulation cascade of indoles with aryldiazonium salts and polyhalomethanes or acetone is presented by dual hydrogen atom transfer (HAT) and C-H functionalization. By employing readily accessible aryldiazonium salts as the radical initiators and electrophiles and polyhalomethanes and acetone as the C1 units, this method unprecedentedly constructs a pyrazole ring on an indole ring skeleton through the formation of two C-N bonds and a C-C bond in a single reaction.

引用

页码：6549 / 6554

页数：6

共 46 条

[31] Iminyl Radical-Triggered 1,5-Hydrogen-Atom Transfer/Heck-Type Coupling by Visible-Light Photoredox Catalysis
Chen, Li
Guo, Li-Na
Ma, Zhi-Yong
Gu, Yu-Rui
Zhang, Junjie
Duan, Xin-Hua
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6475 - 6482
[32] Copper-catalyzed 1,2,2-trifunctionalization of maleimides with 1,7-enynes and oxime esters via radical relay/1,5-hydrogen-atom transfer
Jiang, Li-Lin
Qiu, Hui
Zhou, Yu
Wang, Ling-Tao
Yang, Wen-Hui
Deng, Chao
Wei, Wen-Ting
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (24) : 6096 - 6102
[33] 1,5-hydrogen transfer - A hitherto ignored decay channel in the photodegradation of poly(2,6-dimethyl-1,4-phenylene oxide)
Schneider, S
Gedeck, P
Harrer, J
Richter, F
Clark, T
CHEMICAL PHYSICS LETTERS, 1996, 257 (5-6) : 616 - 621
[34] 1,5-HYDROGEN TRANSFER DURING DIAZONIUM ION DECOMPOSITION .2. FORMATION OF 5- AND 7-MEMBER NITROGEN HETEROCUCLES
COHEN, T
MCKEEVER, LD
DINWOODIE, AH
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (10): : 3385 - &
[35] Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade
Gu, Yu-Rui
Duan, Xin-Hua
Chen, Li
Ma, Zhi-Yong
Gao, Pin
Guo, Li-Na
ORGANIC LETTERS, 2019, 21 (04) : 917 - 920
[36] 1,5-Hydrogen Atom Transfer/Surzur-Tanner Rearrangement: A Radical Cascade Approach for the Synthesis of 1,6-Dioxaspiro[4.5]decane and 6,8-Dioxabicyclo[3.2.1]octane Scaffolds in Carbohydrate Systems
Leon, Elisa, I
Martin, Angeles
Montes, Adrian S.
Perez-Martin, Ines
Rodriguez, Maria del Sol
Suarez, Ernesto
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14508 - 14552
[37] SmI2-induced 2,3-Wittig rearrangement: Regioselective generation of alpha-allyloxy carbanions via 1,5-hydrogen transfer of vinyl radicals
Kunishima, M
Hioki, K
Kono, K
Kato, A
Tani, S
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22): : 7542 - 7543
[38] Cobalt-catalyzed C(sp2)-H/C(sp3)-H coupling via directed C-H activation and 1,5-hydrogen atom transfer
Sun, Qiao
Yoshikai, Naohiko
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04): : 582 - 585
[39] Zwitterionic 1,2,3-Triazolium Amidate as a Catalyst for Photoinduced Hydrogen-Atom Transfer Radical Alkylation
Ohmatsu, Kohsuke
Suzuki, Ryuhei
Furukawa, Yukino
Sato, Makoto
Ooi, Takashi
ACS CATALYSIS, 2020, 10 (04) : 2627 - 2632
[40] Distal Construction of a Carbon-SCF2R Bond on Aliphatic Alcohols Enabled by 1,5-Hydrogen-Atom Transfer
Petit-Cancelier, Fabien
Ruyet, Louise
Couve-Bonnaire, Samuel
Besset, Tatiana
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (08) : 1498 - 1502

← 1 2 3 4 5 →