Efficient Heck Vinylation of Aryl Halides Catalyzed by a New Air-Stable Palladium−Tetraphosphine Complex

Feuerstein, Marie; Doucet, Henri; Santelli, Maurice

doi:10.1021/jo015645b

Cited by 116 publications

(58 citation statements)

References 14 publications

(15 reference statements)

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“…With reactive substrates, such as activated aryl bromides and iodobenzene, TONs up to 10 8 were observed in reactions with acrylates. [176] Styrene gave TONs around 10 5 and n-butyl vinyl ether of around 10 4 . [177] Heteroaryl halides (mostly bromides, some iodides) can also be coupled with styrene and acrylates, but the resulting TONs vary widely (from 20 to ca.…”

Section: ð11þmentioning

confidence: 99%

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

2004

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This review discusses the problems associated with developing high-turnover catalysts for the cross-coupling and Heck reactions. New developments in the area, principally constituted by palladacycles and coordinatively unsaturated Pd catalysts featuring bulky phosphanes of high donicity, are reviewed from a mechanistic and synthetic standpoint, and compared with more traditional catalysts obtained from conventional mono-and polydentate Nand P-based ligands, as well as Pd catalysts without strong ligands, such as Pd colloids or heterogeneous catalysts. Carbene ligands are also briefly presented. Whereas a single, most promising approach to highturnover Pd catalysis cannot presently be defined, it is clear that the new "PdL 1 " catalysts (where L 1 is a monodentate bulky P ligand of high donicity) represent the latest, most important development in Pd research, certainly from the standpoint of scope and probably also from the standpoint of efficiency. High turnovers with these catalysts have been described and their use will certainly increase in the next few years. The review ends with a brief discussion containing practical considerations on how to choose a high TON catalyst for a given Heck or cross-coupling reaction of interest.

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Section: ð11þmentioning

confidence: 99%

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

2004

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“…13.8, 19.3, 30.9, 55.3, 64.3, 114.4, 115.8, 127.3, 129.7, 144.2, 161.4, 167.4. n-Butyl (E)-p-methylcinnamate: Oil; 11 1 H NMR (CDCl 3 , 300 MHz) δ: 0.96 (t, J＝7.4 Hz, 3H), 1. 2H),2H),4.20 (t,J＝6.7 Hz,2H),6.34 (d,J＝16.0 Hz,1H),7.18 (d,J＝8.0 Hz,2H),7.42 (d,J＝8.0 Hz,2H),7.65 (d,J＝16.0 Hz, 1H); 13 C NMR (CDCl 3 , 75 MHz) δ: 13.8, 19.3, 21.5, 30.8, 64.4, 117.3, 128.1, 129.7, 131.9, 140.7, 144.6, 167.3. n-Butyl (E)-o-nitrocinnamate: Oil; (d,J＝15.7 Hz,1H),1H),2H),1H),8.14 (d,J＝ 15.7 Hz,1H); 13 C NMR (CDCl 3 , 75 MHz) δ: 13.6, 19.0, 30.6, 64.5, 123.2, 124.8, 129.0, 130.2, 130.5, 133.5, 139.8, 148.2, 165.8. n-Butyl (E)-3-(3-quinolyl)-acrylate: 13 White solid, m.p. 80-82 ℃; 1 H NMR (CDCl 3 , 300 MHz) δ: 0.98 (t, J＝7.4 Hz, 3H), 2H),2H),4.25 (t,J＝6.7 Hz,2H),6.67 (d,J＝16.1 Hz,1H),1H),7.73 (d,J＝6.9 Hz,1H),7.78 (d,J＝16.1 Hz,1H),7.84 (d,J＝6.3 Hz,1H),8.11 (d,J＝ 8.3 Hz,1H),…”

Section: General Procedures For Heck Reactionmentioning

confidence: 99%

Heck Reactions Catalyzed by Palladium Complex Supported on 4‐Aminopyridine Resin

Pan

2009

Chin. J. Chem.

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“…at 130°C for 40 h), and the coupling of deactivated 4-bromoanisole to n-butyl acrylate with a TON of 82000 (yield 82 %, 10 -3 mol-% cat. at 130°C for 72 h); [31] (3) the Sonogashira cross-coupling of phenylacetylene to 4-bromoacetophenone and 4-bromoanisole with TONs of, respectively, 700000 (yield 70 %, 10 -4 mol-% cat. at 140°C for 20 h) and 3800 (yield 38 %, 10 -2 mol-% cat.…”

Section: Introduction and Scopementioning

confidence: 99%

“…4-Bromoacetophenone/phenylboronic acid g palladacycle 74000 [17] 4-Bromoanisole/phenylboronic acid g 7600 [17] 4-Bromoacetophenone/phenylboronic acid h phosphite palladacyle 1000000 [18] 4-Bromoanisole/phenylboronic acid h 30000 [18] 4-Bromoacetophenone/phenylboronic acid j (biaryl)dialkylphosphane 91000000 [20] 4-tBu-bromobenzene/phenylboronic acid j 18600 [20] 4-Bromoacetophenone/phenylboronic acid f alkyl tetraphosphane 96000000 [28] 4-Bromoanisole/phenylboronic acid f 93000 [28] 4-Bromoacetophenone/phenylboronic acid 18 ferrocenyl tetraphosphane 100000 [b] 4-Bromoanisole/phenylboronic acid 18 77000 [b] 4-Bromoacetophenone/phenylboronic acid Pd(OAc) 2 ligand-free 4800 [31] 4-Bromoanisole/phenylboronic acid Pd(OAc) 2 ligand-free 0 [21] [a] Selected results from the first section, systematic ligand-free studies appeared after 2001. [b] Work reviewed herein.…”

Section: Introduction and Scopementioning

confidence: 99%

Ultra‐Low Catalyst Loading as a Concept in Economical and Sustainable Modern Chemistry: The Contribution of Ferrocenylpolyphosphane Ligands

2007

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The challenge of sustainability in modern chemistry will be met with new technologies and processes provided significant progress is made in several key research areas, such as the expansion of chemistry from renewable feedstock, the design of environmentally benign chemicals and solvents, the minimization of depletive resources, and the development of high‐performance catalysis. In this prospect, ligand chemistry is a pivotal science that links modern‐organic,‐inorganic, ‐organometallic, and ‐coordination chemistry through a vast number of valuable applications, precisely associated to catalysis. We review in this article our recent work on catalysis promoted by original ferrocenyl tetra‐, tri‐, and diphosphane ligands. New concepts, taking advantages of this family of branched multidentate ligands, have led to progress in homogeneous catalysis. The search for catalyst longevity and ultra‐low catalyst loadings (high turnover numbers), on the basis of multidentarity effects and robustness of the ferrocenyl backbone were focused on high‐value palladium‐catalyzed C–C cross‐couplings, such as Heck, Suzuki, and Sonogashira reactions. Low catalyst loading was also explored for C–N cross‐coupling in the allylic amination of achiral substrates. The advantages of this newly born family of ligands in the class of multidentate compounds are discussed in light of the valuable information gathered up to now on their reactivity, structure, and mechanistic behavior.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Efficient Heck Vinylation of Aryl Halides Catalyzed by a New Air-Stable Palladium−Tetraphosphine Complex

Cited by 116 publications

References 14 publications

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

Heck Reactions Catalyzed by Palladium Complex Supported on 4‐Aminopyridine Resin

Ultra‐Low Catalyst Loading as a Concept in Economical and Sustainable Modern Chemistry: The Contribution of Ferrocenylpolyphosphane Ligands

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