Palladium-Catalyzed Carbonylative Homocoupling of 2-Iodophenols for the Synthesis of Symmetrical Xanthones

被引:1
作者
Lokolkar, Manjunath S. [1 ]
Bhanage, Bhalchandra M. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Nathalal Parekh Marg, Mumbai 400019, India
关键词
carbonylation; homocoupling; palladium; xanthones; 2-iodophenols; ONE-STEP SYNTHESIS; H ACTIVATION; DERIVATIVES;
D O I
10.1055/a-2123-9288
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report the palladium-catalyzed carbonylative synthesis of symmetrical xanthones from functionalized 2-iodophenols in a one-pot manner. The protocol involves homocoupling of 2-iodophenols using Pd catalyst, Cs2CO3 as base, with gaseous CO as C1 building block. The simple, ligand-and additive-free strategy provides moderate to good yields of symmetrical xanthones. The reaction was also examined with the combination of 2-hydroxyphenyl boronic acid as another coupling partner. Additionally, this protocol was extended for the synthesis of aryl and alkyl salicylate derivatives by varying the reaction conditions.
引用
收藏
页码:2329 / 2335
页数:7
相关论文
共 47 条
[1]   SYNTHESIS AND BIOSYNTHESIS OF PHYTOXANTHONES [J].
AFZAL, M ;
ALHASSAN, JM .
HETEROCYCLES, 1980, 14 (08) :1173-1205
[2]   Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols [J].
Ai, Han-Jun ;
Zhang, Youcan ;
Zhao, Fengqian ;
Wu, Xiao-Feng .
ORGANIC LETTERS, 2020, 22 (15) :6050-6054
[3]   Synthesis of xanthones from 4-(2-phenoxyphenyl)-1-tosyl-1H-1,2,3-triazole via rhodium-catalyzed annulation/oxidation [J].
Anna ;
Chen, Zhaohang ;
Qiao, Hongwei ;
Gao, Juanhong ;
Zhu, Mengyao ;
Li, Chao .
CATALYSIS COMMUNICATIONS, 2021, 161
[4]   Alternative simple and effective synthesis of (di)benzoxanthones and their functions toward fluorescent dyes [J].
Azuma, Eriko ;
Kuramochi, Kouji ;
Tsubaki, Kazunori .
TETRAHEDRON, 2013, 69 (06) :1694-1699
[5]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[6]   Polysulfated Xanthones: Multipathway Development of a New Generation of Dual Anticoagulant/Antiplatelet Agents [J].
Correia-da-Silva, Marta ;
Sousa, Emilia ;
Duarte, Barbara ;
Marques, Franklim ;
Carvalho, Felix ;
Cunha-Ribeiro, Luis M. ;
Pinto, Madalena M. M. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (15) :5373-5384
[7]   Neuroprotective Xanthone Glycosides from Swertia punicea [J].
Du, Xin-Gang ;
Wang, Wei ;
Zhang, Shi-Ping ;
Pu, Xiao-Ping ;
Zhang, Qing-Ying ;
Ye, Min ;
Zhao, Yu-Ying ;
Wang, Bao-Rong ;
Khan, Ikhlas A. ;
Guo, De-An .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (08) :1422-1426
[8]   Cr(CO)6 Mediated Carbonylative Homo-Coupling of Aryl Iodides: Direct Access to Symmetrical Diarylketones [J].
Etemadi-Davan, Elham ;
Iranpoor, Nasser .
CHEMISTRYSELECT, 2016, 1 (14) :4300-4304
[9]   Ionic Liquid Immobilized on Graphene-Oxide-Containing Palladium Metal Ions as an Efficient Catalyst for the Alkoxy, Amino, and Phenoxy Carbonylation Reactions [J].
Gaikwad, Vinayak V. ;
Saptal, Vitthal B. ;
Harada, Kei ;
Sasaki, Takehiko ;
Nishio-Hamane, Daisuke ;
Bhanage, Bhalchandra M. .
CHEMNANOMAT, 2018, 4 (06) :575-582
[10]   Pd/C catalyzed phenoxycarbonylation using N-formylsaccharin as a CO surrogate in propylene carbonate, a sustainable solvent [J].
Gautam, Prashant ;
Kathe, Prasad ;
Bhanage, Bhalchandra M. .
GREEN CHEMISTRY, 2017, 19 (03) :823-830