s, or keywords if they used Heck-type chemistry in their syntheses, because it became one of basic tools of organic preparations, a natural way to

http://aether.cmi.ua.ac.be/artikels/Artikels%20Gitte/Artikels/Reviews/Heck%20reactie%20Beletskaya%20%20Chem.%20Rev.%20003009.pdf

The heck reaction as a sharpening stone of palladium catalysis.

/pdf/aryl-aryl-bond-formation-one-century-after-the-discovery-of-1jdyxlkwix.pdf

Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

Palladium-catalyzed cross-coupling reactions in total synthesis.

In 2010, Richard Heck, Ei-ichi Negishi, and Akira Suzuki joined the prestigious circle of Nobel Laureate chemists for their roles in discovering and developing highly practical methodologies for C-C bond construction. From their original contributions in the early 1970s the landscape of the strategies and methods of organic synthesis irreversibly changed for the modern chemist, both in academia and in industry. In this Review, we attempt to trace the historical origin of these powerful reactions, and outline the developments from the seminal discoveries leading to their eminent position as appreciated and applied today.

Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize

Selected patented cross-coupling reaction technologies.

In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solven...

The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions

The reaction of N,N-diethylamino-tributyltin with aryl bromides in the presence of a catalytic amount of PdCl2(o-tolyl3P)2 gave N,N-diethylaminobenzene derivatives. The reaction is a new kind of amination different from ones through aryne or SRN1 mechanise

Palladium-catalyzed aromatic amination of aryl bromides with n,n-di-ethylamino-tributyltin

Catalytic allylation of aryl halides with allyltributyltin in the presence of tetrakis(triphenylphosphine)palladium(O) was investigated. The reaction with aryl bromides proceeded efficiently to yield allylbenzenes.

Reactions of allyltin compounds iii. allylation of aromatic halides with allyltributyltin in the presence of tetrakis(triphenylphosphine)palladium(o)

Tributylstannyl alkyl or aryl sulfide and bis(tributylstannyl) sulfide were found to be useful to prepare aryl sulfides in good yields under the usual conditions of the palladium-catalyzed reaction with aryl bromides.

Masanori Kosugi

Papers

The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions

Palladium-catalyzed aromatic amination of aryl bromides with n,n-di-ethylamino-tributyltin

Reactions of allyltin compounds iii. allylation of aromatic halides with allyltributyltin in the presence of tetrakis(triphenylphosphine)palladium(o)

Palladium-catalyzed Reaction of Stannyl Sulfide with Aryl Bromide. Preparation of Aryl Sulfide

Mizoroki-Heck type reaction of organoboron reagents with alkenes and alkynes. A Pd(II)-catalyzed pathway with Cu(OAc)2 as an oxidant.