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Multi-Talented Bismuthinidenes: Double C(sp³)─I Bond Activation Using Single or Two Bi Centers.

Pavel Novák¹, Martin Hejda¹, Roman Jambor¹

¹Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, CZ-532 10, Czech Republic.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|April 30, 2025

Summary

Bismuth complexes with bulky substituents undergo C-I bond activation with dihalomethanes. Reaction outcomes depend on the alkyl group and stoichiometry, yielding diverse organobismuth products.

Keywords:

bismuthinidene bond activation low‐valent p‐block elements oxidative addition pincer ligands

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Area of Science:

Organometallic Chemistry
Main group chemistry
Bismuth chemistry

Background:

Organobismuth compounds are gaining interest due to their unique reactivity.
Exploring the reactivity of low-valent bismuth complexes with organic halides is crucial for synthetic applications.

Purpose of the Study:

To investigate the reactivity of low-valent bismuth complexes with bulky substituents towards dihaloalkanes.
To elucidate the influence of steric bulk and reaction stoichiometry on the C-I bond activation pathways.

Main Methods:

Synthesis and characterization of organobismuth complexes.
Reactions of bismuth complexes with diiodomethane and dihaloethanes.
Stoichiometric control and product isolation.

Main Results:

The bismuth complex [2,6-(DippN=CH)2C6H3]Bi (1Dipp) undergoes double C-I bond activation with CH2I2.
The tert-butyl analogue [2,6-(tBuN=CH)2C6H3]Bi (1tBu) shows stoichiometry-dependent reactivity with CH2I2, yielding dinuclear or mononuclear products.
Reactions with CH2ClX result in the formation of [2,6-(tBuN=CH)2C6H3]Bi(CH2Cl)X.

Conclusions:

Low-valent bismuth complexes with bulky substituents exhibit diverse reactivity towards dihaloalkanes.
Stoichiometry plays a critical role in directing the reaction pathway and product distribution.
These findings expand the synthetic utility of organobismuth compounds.