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On–off allosteric control of a bifunctional catalyst

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A Pt(II) weak-link tweezer and a sulfonate regulator switch a squaramide–amine co-catalyst fully on or off in situ.

Source

A concerted two-prong approach to the <i>in situ</i> allosteric regulation of bifunctional catalysis

McGuirk CM, Mendez-Arroyo J, d'Aquino AI, et al. · Chemical science · 2016

doi.org/10.1039/c6sc01454bRead the full paper ↗7 citationscc by

What they did

Authors assembled a heteroligated Pt(II) tweezer with a squaramide–tertiary amine ligand and a sodium sulfonate hydrogen-bond acceptor, switched it between semi-open and fully closed states with chloride, measured DMA binding by 1H NMR, and timed the Michael addition of nitroethane to β-nitrostyrene.

What they found

The fully closed Na+ complex binds DMA strongly (Ka ≈ 75 558 M−1) while the semi-open state shows no recognition. Closed-state catalysis gives nearly quantitative conversion (TOF = 2.69 × 10−4 s−1), and chloride toggling reverses activity. Embedding the catalyst in the WLA scaffold improves activity versus free ligand.

The limits

What it doesn't show

Scope beyond a few conjugate additions is proposed rather than demonstrated at scale; polymer-length control of lactide ROP is suggested but not shown here.

Key terms

Weak-link approach (WLA)
Hemilabile P,X ligands on d8 metals that open or close a supramolecular catalyst with chemical effectors such as Cl−.
Hydrogen-bond-donating (HBD) catalyst
A squaramide that activates electrophiles by dual hydrogen bonds.
Fully closed (FC) vs semi-open (SO)
Chelated rigid vs flexible P-only states of the Pt(II) tweezer.
Bifunctional HBD–Lewis base
Co-catalyst that activates both electrophile (HBD) and nucleophile (amine).
Allosteric regulation
Activity switched by a remote coordination change rather than by modifying the catalytic site covalently.

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The off state of this tweezer catalyst is the:

Common questions

What turns the catalyst off?

The semi-open state lets the sulfonate hydrogen-bond to the squaramide so substrate cannot bind.

What model reaction was timed?

Michael addition of nitroethane to β-nitrostyrene.

Why does Na+ matter in the closed state?

The cation screens the sulfonate so intermolecular ligand–ligand association is minimized.

Can you switch in situ?

Yes: add and abstract Cl− to toggle FC and SO.

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