A Highly Active Catalyst for Suzuki–Miyaura Cross‐Coupling Reactions of Heteroaryl Compounds

Billingsley, Kelvin L.; Anderson, Kevin W.; Buchwald, Stephen L.

doi:10.1002/anie.200600493

Cited by 363 publications

(180 citation statements)

References 41 publications

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“…[2] These phosphines have been used as ligands for gold, [3][4][5][6][7][8][9][10][11] silver, [12] rhodium, [13,14] ruthenium [15][16][17] and copper [18] where they have been shown to impart improvements in reactivity and catalyst stability. It is in reactions catalyzed by palladium, however, that they have had by far the greatest impact including the Sonogashira, [19] Negishi, [20] Hiyama, [21][22][23] Kumada [24] and Suzuki [25][26][27][28][29][30] cross-coupling reactions, Heck reaction, [31][32][33] enolate arylation [34][35][36][37] and allylation, [38] reductive cyclization [39] and etherification, [40][41][42][43] silylation, [44] borylation, [45][46][47] cyanation, [48,…”

Section: Introductionmentioning

confidence: 99%

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

2008

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Palladium-catalyzed amination of aryl halides has undergone rapid development in the last 12 years. This has been largely driven by implementation of new classes of ligands. Biaryl phosphines have proven to provide especially active catalysts in this context. This review discusses the applications that these catalysts have found in C-N cross-coupling in heterocycle synthesis, pharmaceuticals, materials science and natural product synthesis.

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Section: Introductionmentioning

confidence: 99%

Biaryl Phosphane Ligands in Palladium‐Catalyzed Amination

2008

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“…The molecular framework of these systems can be easily varied in order to fine-tune the ligand properties. 121 It was shown that the catalysts based on S-Phos were not inhibited in the presence of aminopyridines and aminopyrimidines, 122 as found with earlier ligand systems. 123 Various heterocycles including pyrroles, thiophenes, pyrazines, pyridines, quinozalines, indoles, and quinolines have been successfully employed using these systems.…”

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confidence: 67%

ChemInform Abstract: Practical Aspects of Carbon—Carbon Cross‐Coupling Reactions Using Heteroarenes

Slagt

Vries

et al. 2010

ChemInform

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Abstract:The use of cross-coupling reactions for the preparation of alkylated and arylated heteroaromatic compounds has increased tremendously over the past two decades. This has been driven on the one hand by the increasingly complex structures of new drugs, most of which contain one or more heterocyclic motifs. On the other hand, the development of new catalysts and reaction conditions for these reactions has rendered even the most unreactive of heteroarenes amenable to cross-coupling chemistry. Not only have new bulky electron-donating ligands been created that allow the coupling of aryl chlorides under mild conditions, but also the use of ligand-free palladium, in particular at very low doses, sometimes called homeopathic palladium, has served to bring down the cost of these reactions. More recent and enabling developments are the use of catalysts based on cheap metals such as nickel, copper, and iron. Scale-up issues are availability and cost of starting materials, cost of the catalysts (related to cost of the metal and the ligand, intrinsic activity and stability of the catalyst), solvent choice, and removal of the metal to <10 ppm from the final product. This latter point is aggravated with heteroaromatics as they tend to be good ligands for the transition metal. For the same reason substrate and product inhibition are quite common.

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“…202 Another member of this family of natural products has been obtained by palladium-catalyzed coupling of the boron derivative 100 with a pyrrolyl triflate. 203 This pyrrole boronic acid compound has also been employed in other cross-coupling reactions, 204 including progesterone receptor modulators 205 and the total synthesis of ageladine A. 206 When the boronic acid functionality in the protected pyrrole is desired at C-3, its preparation is achieved generally via a brominationlithiation-borination sequence, a recent example being the synthesis of a N-silyl-protected pyrrol-3-ylboronic acid, which has been employed in the synthesis of conductive electrochromic polymers.…”

Section: Aromatic Five-membered Ringsmentioning

confidence: 99%