Synthesis of Polyhedral Borane Cluster Fused Heterocycles via Transition Metal Catalyzed B-H Activation

被引:21
作者
Cao, Ke [1 ]
Zhang, Cai-Yan
Xu, Tao-Tao
Wu, Ji
Wen, Xin-Yu
Jiang, Wen-Jun
Chen, Mao
Yang, Junxiao
机构
[1] Southwest Univ Sci & Technol, State Key Lab Environm Friendly Energy Mat, 59 Qinglong Rd, Mianyang 621010, Sichuan, Peoples R China
来源
MOLECULES | 2020年 / 25卷 / 02期
关键词
carborane; heterocycle; B-H activation; polyhedral borane cluster; O-CARBORANES; MEDICINAL CHEMISTRY; BORON CLUSTERS; DRUG DISCOVERY; BONDS; ARYLATION; ALKENYLATION; SUBSTITUTION; STEPWISE; ACID;
D O I
10.3390/molecules25020391
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Aromatic heterocycles are ubiquitous building blocks in bioactive natural products, pharmaceutical and agrochemical industries. Accordingly, the carborane-fused heterocycles would be potential candidates in drug discovery, nanomaterials, metallacarboranes, as well as photoluminescent materials. In recent years, the transition metal catalyzed B-H activation has been proved to be an effective protocol for selective functionalization of B-H bond of o-carboranes, which has been further extended for the synthesis of polyhedral borane cluster-fused heterocycles via cascade B-H functionalization/annulation process. This article summarizes the recent progress in construction of polyhedral borane cluster-fused heterocycles via B-H activation.
引用
收藏
页数:11
相关论文
共 56 条
[21]   Fusing Carborane Carboxylic Acids with Alkynes: 3D Analogues of Isocoumarins via Regioselective B-H Activation [J].
Lin, Furong ;
Shen, Yunjun ;
Zhang, Yuanbin ;
Sun, Yuji ;
Liu, Jiyong ;
Duttwyler, Simon .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (03) :551-555
[22]   Catalytic Regioselective Cage B(8)-H Arylation of o-Carboranes via "Cage-Walking" Strategy [J].
Lyu, Hairong ;
Zhang, Jie ;
Yang, Jingting ;
Quan, Yangjian ;
Xie, Zuowei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (10) :4219-4224
[23]   Rhodium catalyzed cascade cyclization featuring B-H and C-H activation: one-step construction of carborane-fused N-polyheterocycles [J].
Lyu, Hairong ;
Quan, Yangjian ;
Xie, Zuowei .
CHEMICAL SCIENCE, 2018, 9 (30) :6390-6394
[24]   Transition Metal Catalyzed, Regioselective B(4)-Halogenation and B(4,5)-Diiodination of Cage B-H Bonds in o-Carboranes [J].
Lyu, Hairong ;
Quan, Yangjian ;
Xie, Zuowei .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (59) :14866-14871
[25]   Transition Metal Catalyzed Direct Amination of the Cage B(4)-H Bond in o-Carboranes: Synthesis of Tertiary, Secondary, and Primary o-Carboranyl Amines [J].
Lyu, Hairong ;
Quan, Yangjian ;
Xie, Zuowei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12727-12730
[26]   Rhodium-Catalyzed Regioselective Hydroxylation of Cage B-H Bonds of o-Carboranes with O2 or Air [J].
Lyu, Hairong ;
Quan, Yangjian ;
Xie, Zuowei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) :11840-11844
[27]   Palladium-Catalyzed Direct Dialkenylation of Cage BH Bonds in o-Carboranes through Cross-Coupling Reactions [J].
Lyu, Hairong ;
Quan, Yangjian ;
Xie, Zuowei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (36) :10623-10626
[28]   Boron clusters in luminescent materials [J].
Mukherjee, Sanjoy ;
Thilagar, Pakkirisamy .
CHEMICAL COMMUNICATIONS, 2016, 52 (06) :1070-1093
[29]   Synthesis of alkyl and aryl derivatives of closo-B12H122- by the palladium-catalyzed coupling of closo-B12H11I2- with Grignard reagents [J].
Peymann, T ;
Knobler, CB ;
Hawthorne, MF .
INORGANIC CHEMISTRY, 1998, 37 (07) :1544-1548
[30]   ORDER OF ELECTROPHILIC SUBSTITUTION IN 1,2-DICARBACLOVODODECABORANE(12) AND NUCLEAR MAGNETIC RESONANCE ASSIGNMENT [J].
POTENZA, JA ;
LIPSCOMB, WN ;
VICKERS, GD ;
SCHROEDE.H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (03) :628-&