π-Allylpalladium Complexes in Synthesis: An Update

被引：24

作者：

Parisotto, Stefano ^{[1
]}

Deagostino, Annamaria ^{[1
]}

机构：

[1] Univ Torino, Dept Chem, Via Giuria 7, I-10125 Turin, Italy

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 09期

关键词：

palladium; allyl; Tsuji-Trost; dienes; enantioselective synthesis; palladium precatalyst; PALLADIUM-CATALYZED ALLYLATION; HETEROCYCLIC CARBENE COMPLEXES; SYNERGISTIC CU/PD CATALYSIS; CONJUGATED DIENES; ALLYLIC ALCOHOLS; C-H; 1,3-DIENES; CASCADE; ESTERS; ACTIVATION;

D O I：

10.1055/s-0037-1611745

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review aims to summarize the development of the chemistry of -allylpalladium complexes both as intermediates and catalysts/reagents between 2013 and early 2109. Major attention has been devoted to the synthetic aspect of these versatile intermediates. 1 Introduction 2 -Allylpalladium Complexes Generated from Allyl Electrophiles 2.1 Activated Allylic Compounds 2.2 Unactivated Allylic Compounds: Allylic Alcohols and Hydrocarbons 2.3 Total Syntheses 3 -Allylpalladium Complexes Generated from Dienes 3.1 Conjugated Dienes 3.2 Allenes 4 -Allylpalladium Complexes Exploited as Reactants and Precatalysts 4.1 Allylpalladium-Catalyzed Dehydrogenation 4.2 Allylpalladium-Catalyzed Synthesis of Alkenylboronic Esters 4.3 Allylpalladium-Based Precatalysts 5 Conclusions

引用

页码：1892 / 1912

页数：21

共 96 条

[1] Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes [J].

Abu Deiab, Ghina'a I. ;

Al-Huniti, Mohammed H. ;

Hyatt, I. F. Dempsey ;

Nagy, Emma E. ;

Gettys, Kristen E. ;

Sayed, Sommayah S. ;

Joliat, Christine M. ;

Daniel, Paige E. ;

Vummalaneni, Rupa M. ;

Morehead, Andrew T., Jr. ;

Sargent, Andrew L. ;

Croatt, Mitchell P. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 :384-392

[2] Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles [J].

Adamson, Nathan J. ;

Wilbur, Katherine C. E. ;

Malcolmson, Steven J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2761-2764

[3] Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst [J].

Adamson, Nathan J. ;

Hull, Ethan ;

Malcolmson, Steven J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (21) :7180-7183

[4] Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift [J].

Aparece, Mark D. ;

Gao, Chenpeng ;

Lovinger, Gabriel J. ;

Morken, James P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (02) :592-595

[5] Aqueous-Phase Chemistry of η3-Allylpalladium(II) Complexes with Sulfonated N-Heterocyclic Carbene Ligands: Solvent Effects in the Protolysis of Pd-C Bonds and Suzuki-Miyaura Reactions [J].

Asensio, Juan M. ;

Andres, Roman ;

Gomez-Sal, Pilar ;

de Jesus, Ernesto .

ORGANOMETALLICS, 2017, 36 (21) :4191-4201

[6] Catalytic C-H Allylation and Benzylation of Pyrazoles [J].

Bae, Seri ;

Jang, Ha-Lim ;

Jung, Haeun ;

Joo, Jung Min .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) :690-697

[7] Diastereoselective Synthesis of Dibenzo[b,d]azepines by Pd(II)-Catalyzed [5+2] Annulation of o-Arylanilines with Dienes [J].

Bai, Lu ;

Wang, Yan ;

Ge, Yicong ;

Liu, Jingjing ;

Luan, Xinjun .

ORGANIC LETTERS, 2017, 19 (07) :1734-1737

[8] Highly regio- and stereoselective palladium-catalyzed allene bifunctionalization cascade via π-allyl intermediate [J].

Bai, Tao ;

Yang, Yanhui ;

Janes, Trevor ;

Song, Datong ;

Guo, Zhiqiang .

TETRAHEDRON, 2017, 73 (39) :5784-5793

[9] Bis-Functionalization of 1,3-Dienes through 1,4-Conjugate Addition of Amphiphilic Bis-π-Allyl and Related Palladium Intermediates [J].

Baiju, T. V. ;

Vijayan, Ajesh ;

Joseph, Nayana ;

Preethalayam, Preethanuj ;

Radhakrishnan, K. V. ;

Suresh, E. ;

Yamamoto, Yoshinori .

SYNLETT, 2014, 25 (03) :359-364

[10] Palladium-catalysed regioselective hydroamination of 1,3-dienes: synthesis of allylic amines [J].

Banerjee, Debasis ;

Junge, Kathrin ;

Beller, Matthias .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (04) :368-372

← 1 2 3 4 5 6 7 8 9 10 →