Palladium-Catalyzed Radical Cascade lododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate

被引：95

作者：

Wang, Yu-Qi ^{[1
]}

He, Yu-Tao ^{[1
]}

Zhang, Lu-Lu ^{[1
]}

Wu, Xin-Xing ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 17期

基金：

美国国家科学基金会;

关键词：

COPPER-MEDIATED DIFLUOROMETHYLATION; PERFLUOROALKYL IODIDES; SODIUM DITHIONITE; CYCLIZATION; FLUORINE; ALKENES; ALKYNES; ENYNES; CARBOCYCLIZATION; REAGENT;

D O I：

10.1021/acs.orglett.5b02068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and convenient Pd-catalyzed radical cascade iododifluoromethylation/cyclization of 1,6-enynes with ethyl difluoroiodoacetate is demonstrated. The proposed transformation presents high stereoselectivity under mild and facile reaction conditions, thereby allowing an efficient access to a variety of iodine-containing difluoromethylated pyrrolidines. A possible radical pathway for the transformation is proposed on the basis of the results of control experiments and relevant literature reviews.

引用

页码：4280 / 4283

页数：4

共 50 条

[1] Palladium-Catalyzed Cyclization of 1,6-Enynes
Liu Wenjuan
Chen Pinhong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (07) : 2077 - 2091
[2] PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 1,6-ENYNES AND 1,7-ENYNES
TROST, BM
PFRENGLE, W
URABE, H
DUMAS, J
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1923 - 1924
[3] Palladium-catalyzed tandem cyclization/Suzuki coupling of 1,6-enynes
Zhu, GG
Zhang, ZG
ORGANIC LETTERS, 2003, 5 (20) : 3645 - 3648
[4] Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes
Corkey, Britton K.
Toste, F. Dean
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) : 2764 - +
[5] Palladium-Catalyzed Enantioselective Cyclization of 1,6-Enynes to Access Chiral γ-Butyrolactam
Zhang, Liren
Wang, Yuanfang
Tang, Junlong
Wu, Wanqing
Jiang, Huanfeng
JOURNAL OF ORGANIC CHEMISTRY, 2024, 90 (01): : 894 - 898
[6] Visible-Light-Driven Base-Promoted Radical Cascade Difluoroalkylation-Cyclization-Iodination of 1,6-Enynes with Ethyl Difluoroiodoacetate
Wang, Yan
Liu, Ruyan
Zhou, Pengsheng
Wu, Jianglong
Li, Wenshuang
Wang, Chenyu
Li, Hao
Li, Dianjun
Yang, Jinhui
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (05)
[7] Palladium-catalyzed cyclization reaction of 1,6-enynes and disilanes to synthesize silyl benzofurans
Zhao, Bo
Wang, Tianqiang
Xie, Jinyao
Yu, Guojun
Hu, Guangwei
Qin, Jiaze
Zhang, Chengcheng
Yan, Rulong
CHEMICAL COMMUNICATIONS, 2025,
[8] Palladium-catalyzed tandem cyclization/Suzuki coupling of 1,6-enynes: Reaction scope and mechanism
Zhu, GG
Tong, XF
Cheng, J
Sun, YH
Li, D
Zhang, ZG
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05): : 1712 - 1717
[9] Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives
Babu, Undamatla Suri
Singam, Maneesh Kumar Reddy
Kumar, Muniganti Naveen
Nanubolu, Jagadeesh Babu
Reddy, Maddi Sridhar
ORGANIC LETTERS, 2022, 24 (08) : 1598 - 1603
[10] Palladium-catalyzed cascade cyclization-coupling reactions of 2-bromo-1,6-enynes with organoboronic acids
Oh, CH
Lim, YM
TETRAHEDRON LETTERS, 2003, 44 (02) : 267 - 270

← 1 2 3 4 5 →