Fluorination and hydrolytic stability of water-soluble platinum complexes with a borane-bridged diphosphoramidite ligand

Culpepper, Johnathan D.; Lee, Kyounghoon; Portis, William; Swenson, Dale C.; Daly, Scott R.

doi:10.1039/d2dt01482c

Cited by 1 publication

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References 78 publications

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“…We have observed in other studies that TBDPhos complexes are significantly more stable with respect to pH‐induced decomposition when fluoride is added to boron in the TBD backbone. [ 8c , 18 ] Thus we postulated that addition of fluoride after the Diels–Alder reaction but before switching to the basic conditions required for the Suzuki reactions would attenuate ligand decomposition (Figure 4 ). Addition of ( n Bu 4 N)F (0.5 equiv) after the DA reaction allowed the subsequent Suzuki reaction to proceed smoothly with PhB(OH) 2 to yield 8 b (68 %, dr 97 : 3; Table 5 ).…”

Section: Resultsmentioning

confidence: 99%

Leveraging Metal and Ligand Reactive Sites for One Pot Reactions: Ligand‐Centered Borenium Ions for Tandem Catalysis with Palladium

Skaria

Culpepper

Daly

2022

Chemistry A European J

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Tandem catalysts that perform two different organic transformations in a single pot are highly desirable because they enable rapid and efficient assembly of simple organic building blocks into more complex molecules. Many examples of tandem catalysis rely on metal-catalyzed reactions involving one or more metal complexes. Remarkably, despite surging interest in the development of chemically reactive (i. e., non-innocent) ligands, there are few examples of metal complexes that leverage ligand-centered reactivity to perform catalytic reactions in tandem with separate catalytic reactions at the metal. Here we report how multifunctional Pd complexes with triaminoborane-derived diphosphorus ligands, called TBDPhos, appear to facilitate borenium-catalyzed cycloaddition reactions at the ligand, and Pd-catalyzed Stille and Suzuki cross-coupling reactions at the metal. Both transformations can be accessed in one pot to afford rare examples of tandem catalysis using separate metal and ligand catalysis sites in a single complex.

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Section: Resultsmentioning

confidence: 99%

Leveraging Metal and Ligand Reactive Sites for One Pot Reactions: Ligand‐Centered Borenium Ions for Tandem Catalysis with Palladium

Skaria

Culpepper

Daly

2022

Chemistry A European J

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Fluorination and hydrolytic stability of water-soluble platinum complexes with a borane-bridged diphosphoramidite ligand

Abstract: Here we report the synthesis, characterization, and hydrolytic stability of water-soluble Pt(ii) complexes containing a triaminoborane-bridged diphosphoramidite ligand that can be fluorinated using simple fluoride salts.

Cited by 1 publication

References 78 publications

Leveraging Metal and Ligand Reactive Sites for One Pot Reactions: Ligand‐Centered Borenium Ions for Tandem Catalysis with Palladium

Leveraging Metal and Ligand Reactive Sites for One Pot Reactions: Ligand‐Centered Borenium Ions for Tandem Catalysis with Palladium

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