Multitasking haloalkynes in synthetic chemistry

被引：2

作者：

Chen, Ci ^{[1
]}

Zhang, Qiaoya ^{[1
]}

Li, Yinling ^{[1
]}

Gao, Yang ^{[1
]}

Chen, Qian ^{[1
]}

Huo, Yanping ^{[1
]}

Li, Xianwei ^{[1
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

来源：

TETRAHEDRON LETTERS | 2024年 / 147卷

基金：

美国国家科学基金会;

关键词：

Haloalkynes; Transition-metal catalysis; Divergent reactivity; Synthetic chemistry; PALLADIUM-CATALYZED BROMOALKYNYLATION; C-H ACTIVATION; C(SP(3))-H BONDS; ALKYNYLATION; ETHYNYLATION; HETEROCYCLES; ISOCYANIDES; AMINATION; ENTRY;

D O I：

10.1016/j.tetlet.2024.155229

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Haloalkynes that could be accessed from diverse precursors, are versatile in synthetic chemistry as alkynylation and/or halogenation reagents, enabling concise and divergent delivery of functional molecules in selective manners. Recently, additional reactivity and substrate scope of haloalkynes, was also developed, facilitating expedient delivery of fused heterocycles.

引用

页数：8

共 69 条

[1] Palladium-catalyzed 1,1-alkynylbromination of alkenes with alkynyl bromides [J].

Ano, Yusuke ;

Kawai, Natsuki ;

Chatani, Naoto .

CHEMICAL SCIENCE, 2021, 12 (37) :12326-12332

[2] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986

[3] Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes [J].

Bai, Yu-Bin ;

Luo, Zaigang ;

Wang, Yuguang ;

Gao, Jin-Ming ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (17) :5860-5865

[4] Ruthenium-Catalyzed trans-Hydroalkynylation and trans-Chloroalkynylation of Internal Alkynes [J].

Barsu, Nagaraju ;

Leutzsch, Markus ;

Fuerstner, Alois .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (44) :18746-18752

[5] Synthesis and evaluation of a series of C3-substituted CBI analogues of CC-1065 and the duocarmycins [J].

Boger, DL ;

Brunette, SR ;

Garbaccio, RM .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :5163-5173

[6] Electrophilic alkynylation: the dark side of acetylene chemistry [J].

Brand, Jonathan P. ;

Waser, Jerome .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179

[7] Formal Inverse Sonogashira Reaction: Direct Alkynylation of Arenes and Heterocycles with Alkynyl Halides [J].

Dudnik, Alexander S. ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) :2096-2098

[8] Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement [J].

Elena de Orbe, M. ;

Zanini, Margherita ;

Quinonero, Ophelie ;

Echavarren, Antonio M. .

ACS CATALYSIS, 2019, 9 (09) :7817-7822

[9] A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].

Frederick, MO ;

Mulder, JA ;

Tracey, MR ;

Hsung, RP ;

Huang, J ;

Kurtz, KCM ;

Shen, LC ;

Douglas, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369

[10] Ligand-Enabled Alkynylation of C(sp3)-H Bonds with Palladium(II) Catalysts [J].

Fu, Haiyan ;

Shen, Peng-Xiang ;

He, Jian ;

Zhang, Fanglin ;

Li, Suhua ;

Wang, Peng ;

Liu, Tao ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (07) :1873-1876

← 1 2 3 4 5 6 7 →