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Schnyder, Anita; Indolese, Adriano F.; Studer, Martin; Blaser, Hans‐Ulrich

doi:10.1002/1521-3757(20021004)114:19<3820::aid-ange3820>3.0.co;2-i

Cited by 76 publications

(57 citation statements)

References 6 publications

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“…36,61,62 The selective monoarylation of 3,4-dichloro-2(5H)-furanone at C-4 was, however, achieved using the catalyst system consisting of 2.5 mol% Pd 2 (dba) 3 and 10 mol% P(o-tolyl) 3 . 36,61 Although the use of electron-rich trialkylphosphines as ligands for palladium-catalysed Suzuki reactions has permitted the participation of challenging electrophiles such as deactivated aryl chlorides, the use of these phosphines, especially for large-scale applications, is limited by the fact that these commercially available ligands cannot be readily handled in air because of the ease with which they undergo oxidation. However, in 2001, one of these ligands, P(t-Bu) 3 , was converted into the air-stable phosphonium salt [(t-Bu) 3 PH]BF 4 .…”

Section: Methodsmentioning

confidence: 71%

Untitled

2004

Synthesis

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This review with 206 references covers the literature published until March 2004 on the development and applications of new efficient catalyst systems for the Suzuki palladium-catalysed cross-coupling reaction of organoboron compounds with organic electrophiles. Where possible, the relative advantages of the new catalyst systems in this synthetically very important carbon-carbon bond forming reaction have been compared.

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Section: Methodsmentioning

confidence: 71%

Untitled

2004

Synthesis

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“…In some of these cases, a possible involvement of oxidation states +II and +IV in the catalytic cycle has been considered [25]. Similarly, other palladacycles such as 3 [26e,h] or 6 [27] have been used in the Heck reactions (Figure 8.1) [24,26,28]. It has been proposed that, at least for NC palladacycles, the reaction proceeds through the classical phosphine-free Pd(0)/Pd(II) catalytic cycle and that the active catalysts are actually slowly formed palladium clusters [29].…”

Section: 22 the Catalystsmentioning

confidence: 99%

Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

Bräse¹,

Meijere²

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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The carbopalladation of an alkene by an organylpalladium halide is the essential step in one of the major contemporary metal-catalyzed C-C coupling reactions. About 45 years ago, a Japanese and an American group almost simultaneously designed and executed palladium-mediated coupling reactions of aryl and alkenyl halides with alkenes [1]. In subsequent investigations, Richard Heck and his group developed this reaction into a catalytic transformation and started to demonstrate its usefulness as well as its rather broad scope. The real push to utilize this powerful C-C-bondforming process, however, started only around the mid-1980s, and by now, an impressive number of publications have established the meanwhile so-called Heck reaction [2] 1) as an indispensable method in Organic Synthesis [3][4][5][6][7]. The universal recognition of the importance of the Heck reaction and the Negishi as well as the Suzuki coupling eventually won the Nobel Prize for Richard Heck along with Ei-ichi Negishi and Akira Suzuki in 2010. The applications of the Heck reaction range from the preparation of -functionalized and unfunctionalized -hydrocarbons, novel polymers, and dyes to new advanced enantioselective syntheses of natural products and biologically active nonnatural compounds. The more or less simultaneous developments of mechanistically related variants, namely, the Kumada, Suzuki, Stille, Hiyama, and Negishi coupling reactions (Chapters 12, 2, 3, 4, and 15, respectively) of metallated alkenes and arenes with aryl and alkenyl halides or the metal-catalyzed formation and cycloisomerization of enynes have drawn profit from the improvement of and mechanistic insights into the Heck reaction. This, of course, applies vice versa as well. Using only a catalytic amount of a palladium(0) complex or a precursor to a palladium species, the Heck reaction can bring about unprecedented structural changes, particularly when conducted intramolecularly. The full potential of this palladium-catalyzed process is still being further explored as demonstrated by a total of over 7000 publications in the past 40 years by 1) The alkynylation of aryl and alkenyl halides, frequently also considered as Heck reactions, is described in Chapter 6.

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“…Here the metal is in the oxidation state +2 and needs to be reduced to ±0 to enter the catalytic cycle. Generally, the nitrogen 13 Prashad [31] and Hartwig [32] Nolan [33] Blaser [34] Buchwald [35,36] compound serves as the reducing agent; here, amines that possess β-hydrogen atoms are suitable for fast reduction. For substrates lacking β-hydrogen atoms, this process may be slow, and the addition of an activator (e.g., NEt 3 , iPr 2 NH, or catalytic amounts of boronic acid [24d]) may be necessary.…”

Section: Choice Of Precatalystmentioning

confidence: 99%

Palladium‐Catalyzed Aromatic Carbon–Nitrogen Bond Formation

Paradies

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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Cited by 76 publications

References 6 publications

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Cross‐Coupling of Organyl Halides with Alkenes – The Heck Reaction

Palladium‐Catalyzed Aromatic Carbon–Nitrogen Bond Formation

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