[4+2] Annulation Cascades of 2-Bromo-1-arylpropan-1-ones with Terminal Alkynes Involving C-Br/C-H Functionalization

被引：14

作者：

Ouyang, Xuan-Hui ^{[1
]}

Hu, Chao ^{[1
]}

Song, Ren-Jie ^{[1
]}

Li, Jin-Heng ^{[1
,2
]}

机构：

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

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

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 15期

关键词：

HECK-TYPE REACTION; VISIBLE-LIGHT; RADICAL ALKENYLATION; METALLAPHOTOREDOX CATALYSIS; TANDEM CYCLIZATION; BROMIDES; ALKENES; HALIDES; CARBOCYCLIZATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.8b01962

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Straightforward access to various substituted naphthalenones by copper-catalyzed [4 + 2] annulation cascades of 2-bromo-l-arylpropan-1-ones with terminal alkynes is presented. Employing a Cu(MeCN)(4)PF4 catalyst and 1,10-phenanthroline (1,10-Phen) ligand enables the formation of three new C-C bonds in a single reaction via [4 + 2] annulation of a 2-bromo-1-arylpropan-1-one with an alkyne followed by alpha-alkylation with the other 2-bromo-1-arylpropan-1-one with excellent functional group tolerance and step efficiency.

引用

页码：4659 / 4662

页数：4

共 50 条

[31] Rh(iii)-Catalyzed switchable C-H functionalization of 2-(1H-pyrazol-1-yl)pyridine with internal alkynes
Wu, Shaonan
Wang, Zhuo
Ma, Dianxue
Chen, Chen
Zhu, Bolin
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09) : 1158 - 1163
[32] Rh/Cu-Catalyzed Cascade [4+2] Vinylic C-H O-Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air
Zhao, Yinsong
Li, Shiqing
Zheng, Xuesong
Tang, Junbin
She, Zhijie
Gao, Ge
You, Jingsong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4286 - 4289
[33] SELECTIVE HYDROLYSIS OF C-BR LINKAGE IN 1,2,3-TRI-O-BENZOYL-4-BROMO-4-DEOXY-L-ERYTHRITOL
ZIDERMAN, I
CARBOHYDRATE RESEARCH, 1971, 17 (01) : 220 - &
[34] Palladium-Catalyzed Tandem Dehydrogenative [4+2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations
Sun, Manman
Chen, Weida
Xia, Xiangyu
Shen, Guodong
Ma, Yongmin
Yang, Jianguo
Ding, Hanfeng
Wang, Zhiming
ORGANIC LETTERS, 2020, 22 (08) : 3229 - 3233
[35] Rhodium catalyzed C-H activation and hydroamination in a highly selective redox [4+2] imine/alkyne annulation
Manan, Rajith
Zhao, Pinjing
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[36] Synthesis of Selenopyrano[2,3-c]pyrazol-4(1H)-ones and Their C-H Activation
Choi, In-Hui
Jalani, Hitesh B.
Jeong, Jin-Hyun
SYNLETT, 2021, 32 (03) : 321 - 325
[37] Direct Synthesis of Benzo[c]carbazoles by Pd-Catalyzed C-H [4+2] Annulation of 3-Arylindoles with External 1,3-Dienes
Gerardin, Baptiste
Traboulsi, Iman
Pal, Suman
Lebunetelle, Gabrielle
Ramondenc, Yvan
Hoarau, Christophe
Schneider, Cedric
ORGANIC LETTERS, 2022, : 8164 - 8169
[38] Accessing Polycyclic Heteroarenes Enabled by Copper-Catalyzed Aerobic Oxidative C-H/C-H [4+2] Annulation of 3-Arylindole Derivatives
Yue, Yuanyuan
Yang, Yan
Sun, Chunying
Chao, Junli
Ye, Yaqing
Guo, Xiaohui
Liu, Jianming
ORGANIC LETTERS, 2022, 24 (02) : 478 - 483
[39] Recent Advances on the Catalytic Functionalization of Quinoxalin-2(1H)-ones via C-H Bond Activation
Mao, Pu
Zhu, Junliang
Yuan, Jinwei
Yang, Liangru
Xiao, Yongmei
Zhang, Changsen
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (06) : 1529 - 1547
[40] Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes
Wang, Yan
Shi, Sijia
Zhang, Wei
Nian, Yong
Wu, Xiaowei
ORGANIC LETTERS, 2024, 26 (02) : 483 - 487

← 1 2 3 4 5 →