Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents

被引:19
作者
Shetgaonkar, Samata E. [1 ]
Mamgain, Ritu [1 ]
Kikushima, Kotaro [2 ]
Dohi, Toshifumi [2 ]
Singh, Fateh V. [1 ]
机构
[1] Vellore Inst Technoloy Chennai, Sch Adv Sci SAS, Chem Div, Chennai 600127, Tamil Nadu, India
[2] Ritsumeikan Univ, Coll Pharmaceut Sci, 1-1-1 Nojihigashi, Shiga 5250058, Japan
关键词
palladium; hypervalent iodine reagents; oxidant; catalyst; bond formation; C-H BONDS; C(SP(2))-H BONDS; DIRECTING GROUP; INTERMOLECULAR AMINOACETOXYLATION; OXIDATIVE REARRANGEMENTS; UNACTIVATED C(SP(3))-H; CYCLIZATION-OXIDATION; COUPLING REACTIONS; TERMINAL OLEFINS; DIRECT ARYLATION;
D O I
10.3390/molecules27123900
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
The chemistry of polyvalent iodine compounds has piqued the interest of researchers due to their role as important and flexible reagents in synthetic organic chemistry, resulting in a broad variety of useful organic molecules. These chemicals have potential uses in various functionalization procedures due to their non-toxic and environmentally friendly properties. As they are also strong electrophiles and potent oxidizing agents, the use of hypervalent iodine reagents in palladium-catalyzed transformations has received a lot of attention in recent years. Extensive research has been conducted on the subject of C-H bond functionalization by Pd catalysis with hypervalent iodine reagents as oxidants. Furthermore, the iodine(III) reagent is now often used as an arylating agent in Pd-catalyzed C-H arylation or Heck-type cross-coupling processes. In this article, the recent advances in palladium-catalyzed oxidative cross-coupling reactions employing hypervalent iodine reagents are reviewed in detail.
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页数:57
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共 141 条
[1]   The role of hypervalent iodine(iii) reagents in promoting alkoxylation of unactivated C(sp3)-H bonds catalyzed by palladium(ii) complexes [J].
Abdolalian, Payam ;
Tizhoush, Samaneh K. ;
Farshadfar, Kaveh ;
Ariafard, Alireza .
CHEMICAL SCIENCE, 2021, 12 (20) :7185-7195
[2]   Stereoselective Intermolecular Allylic C-H Trifluoroacetoxylation of Functionalized Alkenes [J].
Alam, Rauful ;
Pilarski, Lukasz T. ;
Pershagen, Elias ;
Szabo, Kalman J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (21) :8778-8781
[3]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[4]   Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review [J].
Biffis, Andrea ;
Centomo, Paolo ;
Del Zotto, Alessandro ;
Zeccal, Marco .
CHEMICAL REVIEWS, 2018, 118 (04) :2249-2295
[5]   Terminal Olefins to Linear α,β-Unsaturated Ketones: Pd(II)/Hypervalent Iodine Co-catalyzed Wacker Oxidation-Dehydrogenation [J].
Bigi, Marinus A. ;
White, M. Christina .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) :7831-7834
[6]   Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones [J].
Chaudhari, Dipali A. ;
Fernandes, Rodney A. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05) :2113-2121
[7]   Oxidant-Controlled Stereoselectivity in the Pd-Catalyzed Allylic Oxidation of cis-Vinylsilanes [J].
Check, Christopher T. ;
Henderson, William H. ;
Wray, Brenda C. ;
Eynden, Matthew J. Vanden ;
Stambuli, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (46) :18503-18505
[8]   Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers [J].
Chen, Fa-Jie ;
Zhao, Sheng ;
Hu, Fang ;
Chen, Kai ;
Zhang, Qi ;
Zhang, Shuo-Qing ;
Shi, Bing-Feng .
CHEMICAL SCIENCE, 2013, 4 (11) :4187-4192
[9]   Divergent Synthesis of 2-Aminofurans via Palladium-Catalyzed Acetoxylative, Alkoxylative, and Hydroxylative Cycloisomerization of Homoallenyl Amides [J].
Cheng, Cungui ;
Liu, Shuiyou ;
Zhu, Gangguo .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) :7604-7612
[10]   Palladium-Catalyzed Intermolecular Aminocarbonylation of Alkenes: Efficient Access of β-Amino Acid Derivatives [J].
Cheng, Jiashun ;
Qi, Xiaoxu ;
Li, Ming ;
Chen, Pinhong ;
Liu, Guosheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (07) :2480-2483