Zirconium-Mediated Synthesis of a New Class of 1,4-Bis(diphenylphosphino)-1,3-butadiene-Bridged Diphosphine, NUPHOS:  Highly Efficient Catalysts for Palladium-Mediated Cross Couplings

Doherty, Simon; Knight, Julian G.; Robins, Edward G.; Scanlan, Tom H.; Champkin, Paul A.; Clegg, William

doi:10.1021/ja010090n

Cited by 53 publications

(13 citation statements)

References 13 publications

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“…Detailed analysis of these helically chiral molecules revealed that the dienes were fluxional in solution. Analogous diene structures could be assembled by the zirconium‐mediated reductive cyclization of diynes 11a. Doherty, Knight, and co‐workers prepared a series of bisphosphines by this method 11.…”

Section: Methodsmentioning

confidence: 99%

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Copper‐Catalyzed Trifluoromethyl Thiolation—Mild and Efficient Synthesis of Trifluoromethyl Thioethers

Rueping

Tolstoluzhsky

Nikolaienko

2013

Chemistry A European J

108

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Mild-mannered sulfur: A general method for the synthesis of vinyl trifluoromethyl thioethers starting from readily available di-, tri-, and tetrasubstituted vinyl iodides was developed. A wide variety of substrates were applied in the reaction with CuSCF3 to give the corresponding products in high yields, within short reaction times, with retention of the initial E/Z isomer ratio. In addition, a copper-catalyzed trifluoromethyl thioether protocol has been also developed.

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Section: Methodsmentioning

confidence: 99%

“…Bisphosphine 2 was prepared from 1,2‐bis(2‐butynyl)benzene by a simple one‐pot operation based on a reported method 11a. Subsequent oxidation of 2 with H 2 O 2 afforded phosphine oxide 1 in quantitative yield (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Trifluoromethyl Thiolation—Mild and Efficient Synthesis of Trifluoromethyl Thioethers

Rueping

Tolstoluzhsky

Nikolaienko

2013

Chemistry A European J

108

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“…In 2001 a new class of di-alkenylphosphines, the Nuphos family, appeared in the literature [51]. These compounds having a 1,4-bis(diphenylphosphino)butadiene backbone (96a or 96b) were complexed to PdCl 2 and used in the model cross-coupling reaction between bromobenzene or 2-bromopropene and s-BuMgCl (eq.…”

Section: Pre-formed Alkenylphosphine Catalystsmentioning

confidence: 99%

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

Julienne¹,

Toulgoat²,

Delacroix

et al. 2010

COC

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Alkenylphosphines are compounds of great interest in view of their structures. The most interesting feature is the carboncarbon double bond, which is directly linked to the phosphorus atom. Nucleophilic addition or cycloaddition reactions can take place at this unsaturation, which can also be used as a coordinating part in the presence of a metal. Thus, alkenylphosphines have found numerous applications in various fields of chemistry. They are useful intermediates in organic synthesis: numerous studies are devoted to their transformation into bidentate ligands, to their use as precursors for dendrimer and polymer chemistry or as ligand for homogeneous catalysis. Due to the presence of both the phosphorus atom and the carbon-carbon double bond, they are also of great interest in coordination chemistry and their different bonding modes have been largely documented. Moreover, after complexation to transition metal, a great amount of work has been carried out on their reactivity in cycloaddition reactions, as well as in functionalization of the carbon-carbon double bond and other miscellaneous reactions. These main applications will be reviewed hereafter.

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“…A zirconium-mediated synthesis of a new class of ligands, namely 1,4-bis(diphenylphosphino)-1,3-butadiene-bridged diphosphine (NUPHOS, 38), from alkynes (39a and 39b), has been reported. 13 The diphosphine is prepared by transmetallation of the zirconocycle 40 to copper to give a divinylcopper species 41, which is quenched with chlorodiphenylphosphine to afford 1,2,3,4-Ph 4 -NUPHOS (38a) or 1,2,3,4-Me 4 -NUPHOS (38b), depending on the choice of alkyne, Scheme 11.…”

Section: Hydrozirconation the Hydrozirconation Of Internal And Termin...mentioning

confidence: 99%

3 Transition metals in organic synthesis : Part (ii) Stoichiometric applications

Fairlamb

2002

Annu. Rep. Prog. Chem., Sect. B: Org. Chem.

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Zirconium-Mediated Synthesis of a New Class of 1,4-Bis(diphenylphosphino)-1,3-butadiene-Bridged Diphosphine, NUPHOS: Highly Efficient Catalysts for Palladium-Mediated Cross Couplings

Cited by 53 publications

References 13 publications

Copper‐Catalyzed Trifluoromethyl Thiolation—Mild and Efficient Synthesis of Trifluoromethyl Thioethers

Copper‐Catalyzed Trifluoromethyl Thiolation—Mild and Efficient Synthesis of Trifluoromethyl Thioethers

Alkenylphosphines: Applications in Synthesis, Catalysis and Coordination Chemistry

3 Transition metals in organic synthesis : Part (ii) Stoichiometric applications

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