Palladium-Catalyzed Annulation of Internal Alkynes: Direct Access to π-Conjugated Ullazines

被引：36

作者：

Wan, Danyang ^{[1
,2
]}

Li, Xiaoyu ^{[1
,2
]}

Jiang, Ruyong ^{[1
,2
]}

Feng, Boya ^{[1
,2
]}

Lan, Jingbo ^{[1
,2
]}

Wang, Ruilin ^{[3
]}

You, Jingsong ^{[1
,2
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, 29 Wangjiang Rd, Chengdu 610064, Peoples R China

[2] Sichuan Univ, West China Med Sch, State Key Lab Biotherapy, 29 Wangjiang Rd, Chengdu 610064, Peoples R China

[3] Sichuan Univ, Coll Mat Sci & Engn, 29 Wangjiang Rd, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 12期

关键词：

C-H ACTIVATION; OXIDATIVE ANNULATION; SOLAR-CELLS; HYDROCARBONS; HETEROARENES; MOLECULES; ARYLATION; DESIGN; BONDS;

D O I：

10.1021/acs.orglett.6b01182

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various p-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C-H functionalization in the construction of organic optoelectronic materials.

引用

页码：2876 / 2879

页数：4

共 50 条

[41] PALLADIUM-CATALYZED HYDROCARBOXYLATION OF ALKYNES
ZARGARIAN, D
ALPER, H
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 319 - INOR
[42] Expedient Synthesis of Functionalized Conjugated Enynes: Palladium-Catalyzed Bromoalkynylation of Alkynes
Li, Yibiao
Liu, Xiaohang
Jiang, Huanfeng
Feng, Zhenning
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (19) : 3338 - 3341
[43] Palladium-Catalyzed Regioselective [3+2] Annulation of Internal Alkynes and Iodo-pyranoquinolines with Concomitant Ring Opening
Aggarwal, Trapti
Jha, Rajeev R.
Tiwari, Rakesh K.
Kumar, Sonu
Kotla, Siva K. Reddy
Kumar, Sushil
Verma, Akhilesh K.
ORGANIC LETTERS, 2012, 14 (20) : 5184 - 5187
[44] Palladium-Catalyzed Denitrogenative Coupling of Aryldiazonium Salts with Terminal Alkynes for the Assembly of Internal Alkynes
Guo, Ziyang
Xiong, Xun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (40)
[45] Highly stereoselective heterogeneous palladium-catalyzed transfer semihydrogenation of internal alkynes to access cis-alkenes
Huang, Wencheng
Li, Jianying
Chen, Qiurong
Cai, Mingzhong
JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (5-6) : 189 - 195
[46] Palladium-catalyzed carbonylative annulation of terminal alkynes: synthesis of coumarins and 2-quinolones
Kadnikov, DV
Larock, RC
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) : 425 - 435
[47] Palladium-Catalyzed Annulation of 2,2′-Diiodobiphenyls with Alkynes: Synthesis and Applications of Phenanthrenes
Lin, Yu-De
Cho, Chun-Lung
Ko, Chih-Wei
Pulte, Anna
Wu, Yao-Ting
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 9979 - 9988
[48] Palladium-catalyzed decarbonylative annulation of phthalimides with arynes: direct construction of phenanthridinones
Meng, Yan-Yu
Si, Xiao-Ju
Song, Yuan-Yuan
Zhou, Hui-Min
Xu, Fen
CHEMICAL COMMUNICATIONS, 2019, 55 (64) : 9507 - 9510
[49] Palladium-catalyzed annulation of monosubstituted β-diketones
Buono, F
Tenaglia, A
SYNLETT, 1998, (10) : 1153 - +
[50] Palladium-Catalyzed Direct Annulation of Benzoic Acids with Phenols to Synthesize Dibenzopyranones
Wang, Yang
Gu, Jie-Yu
Shi, Zhang-Jie
ORGANIC LETTERS, 2017, 19 (06) : 1326 - 1329

← 1 2 3 4 5 →