Propargylic Alcohols as Coupling Partners in Transition-Metal-Catalyzed Arene C-H Activation

被引:57
作者
Kumar, Gadi Ranjith [1 ,2 ,3 ]
Rajesh, Manda [4 ]
Lin, Shuimu [1 ,2 ,3 ]
Liu, Shouping [1 ,2 ,3 ]
机构
[1] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Peoples R China
[2] Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Peoples R China
[3] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Peoples R China
[4] CSIR Indian Inst Chem Technol, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
基金
中国国家自然科学基金;
关键词
Propargylic alcohols; Arene C-H activation; transition metal catalysts; Annulation; Additions; 4+1 ANNULATION; BOND FUNCTIONALIZATION; INTERNAL OXIDANT; O BOND; CYCLIZATION; REACTIVITY; BENZAMIDES; CLEAVAGE; ALKYNES; ACCESS;
D O I
10.1002/adsc.202000896
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Transition-metal-catalyzed site selective arene C-H bond activation concomitant functionalization with various coupling partners gain magnificent attraction in synthetic organic chemistry as complementary to traditional transformations. Mechanistically, these C-H functionalization approaches involve directing group assisted concerted metalation-deprotonation (CMD), migratory insertion, and reductive elimination sequences. In this realm, diverse categories of coupling partners were employed as C-H functionalization buddies. Particularly alkynes gain enormous attention as annulating agents. These units coordinates with metalcycle through pi-interaction produce annulation outcomes in a straightforward manner. Very recently, propargylic alcohols were appointed as valuable archetypes in arene C-H activation armoury, as they have shown regio- and chemoselective migratory insertion into primary metalcycle species via hydroxy chelation. The influential regioselectivity was drawn by dual coordination of metal complexes with the pendent directing group and a propargylic hydroxyl group. In this review, we focused on annulations and functionalization of arenes and propargylic alcohols, which afford intricate cycles as well as complex acyclic motifs in a trouble-free manner. We categorized these transformations based on number of atoms of propargylic alcohols involved in annulation along with some addition reactions. We anticipate to pave a way towards enhanced endeavours for discovering novel reaction avenues.
引用
收藏
页码:5238 / 5256
页数:19
相关论文
共 81 条
[1]  
[Anonymous], 2017, ANGEW CHEM
[2]   Ruthenium(II)-Catalyzed Regioselective-Controlled Allenylation/Cyclization of Benzimides with Propargyl Alcohols [J].
Anukumar, Adapa ;
Tamizmani, Masilamani ;
Jeganmohan, Masilamani .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) :8567-8580
[3]   Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis [J].
Ayers, Benjamin James ;
Chan, Philip Wai Hong .
SYNLETT, 2015, 26 (10) :1305-1339
[4]   Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives [J].
Bauer, Eike B. .
SYNTHESIS-STUTTGART, 2012, 44 (08) :1131-1151
[5]   Hydroxyl Group-Prompted and Iridium(III)-Catalyzed Regioselective C-H Annulation of N-phenoxyacetamides with Propargyl Alcohols [J].
Chen, Weijie ;
Liu, Fu-Xiaomin ;
Gong, Wanchun ;
Zhou, Zhi ;
Gao, Hui ;
Shi, Jingjing ;
Wu, Bo ;
Yi, Wei .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) :2470-2475
[6]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[7]  
Delord J. W., 2015, TOP ORGANOMETAL CHEM, V55, P1
[8]   Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C-H Activation [J].
Fukui, Yuki ;
Liu, Ping ;
Liu, Qiang ;
He, Zhi-Tao ;
Wu, Nuo-Yi ;
Tian, Ping ;
Lin, Guo-Qiang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15607-15614
[9]   Regio- and stereoselective homocoupling of γ-arylated tert-propargyl alcohols with liberation of a ketone molecule and successive cyclization to produce fluorescent dihydrofuran derivatives [J].
Funayama, A ;
Satoh, T ;
Miura, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (44) :15354-15355
[10]   3d Transition Metals for C-H Activation [J].
Gandeepan, Parthasarathy ;
Mueller, Thomas ;
Zell, Daniel ;
Cera, Gianpiero ;
Warratz, Svenja ;
Ackermann, Lutz .
CHEMICAL REVIEWS, 2019, 119 (04) :2192-2452