Multi‐Talented Bismuthinidenes: Double C(<i>sp</i><sup>3</sup>)─I Bond Activation Using Single or Two Bi Centers.

The reaction of [2,6-(DippN = CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi (1Dipp, Dipp = 2,6-iPrC<sub>6</sub>H<sub>3</sub>) with CH<sub>2</sub>I<sub>2</sub> proceeded via double C─I bond activation yielding [2,6-(DippN = CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(μ-(Bi,N)─CH<sub>2</sub>)I<sub>2</sub> (3). By contrast, the reaction of 1Dipp with 1,2-diiodoethane provided [2,6-(DippN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]BiI<sub>2</sub> (1DippI<sub>2</sub>) and ethene. The tert-butyl analogue [2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi (1tBu) reacted with CH<sub>2</sub>ClX to give [2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(CH<sub>2</sub>Cl)X (X═I (4) or Cl (5)). Further, its reactivity with CH<sub>2</sub>I<sub>2</sub> was sensitive towards the stoichiometry since using a 1:1 ratio gave a mixture of dinuclear complex {[2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(I)}<sub>2</sub>(μ-(Bi,Bi)─CH<sub>2</sub>) (6) and [2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(CH<sub>2</sub>I)I (7). The reaction could be shifted in favor of 7 using an excess of CH<sub>2</sub>I<sub>2</sub>, but with 0.45 eq. of CH<sub>2</sub>I<sub>2</sub> compound 6, as a product of double C─I bond activation mediated by two Bi atoms was isolated as the main product.

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Journal
Chemistry - A European Journal
Published
2025-04-30
DOI
https://doi.org/10.1002/chem.202500620
Primary Topic
Synthesis and characterization of novel inorganic/organometallic compounds
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article
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article

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

Roman Jambor, Pavel Novák, Martin Hejda, Libor Dostál et al.
Chemistry - A European Journal
Synthesis and characterization of novel inorganic/organometallic compounds
article

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

Roman Jambor, Pavel Novák, Martin Hejda, Libor Dostál, Alexandre Gagnon, Aleš Růžička
article en

Abstract

The reaction of [2,6-(DippN = CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi (1Dipp, Dipp = 2,6-iPrC<sub>6</sub>H<sub>3</sub>) with CH<sub>2</sub>I<sub>2</sub> proceeded via double C─I bond activation yielding [2,6-(DippN = CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(μ-(Bi,N)─CH<sub>2</sub>)I<sub>2</sub> (3). By contrast, the reaction of 1Dipp with 1,2-diiodoethane provided [2,6-(DippN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]BiI<sub>2</sub> (1DippI<sub>2</sub>) and ethene. The tert-butyl analogue [2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi (1tBu) reacted with CH<sub>2</sub>ClX to give [2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(CH<sub>2</sub>Cl)X (X═I (4) or Cl (5)). Further, its reactivity with CH<sub>2</sub>I<sub>2</sub> was sensitive towards the stoichiometry since using a 1:1 ratio gave a mixture of dinuclear complex {[2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(I)}<sub>2</sub>(μ-(Bi,Bi)─CH<sub>2</sub>) (6) and [2,6-(tBuN═CH)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>]Bi(CH<sub>2</sub>I)I (7). The reaction could be shifted in favor of 7 using an excess of CH<sub>2</sub>I<sub>2</sub>, but with 0.45 eq. of CH<sub>2</sub>I<sub>2</sub> compound 6, as a product of double C─I bond activation mediated by two Bi atoms was isolated as the main product.

Chemistry - A European JournalVol. 31(33)
University of Pardubice (CZ), Université du Québec à Montréal (CA)
Openalex Percentile: Top 92%
Synthesis and characterization of novel inorganic/organometallic compounds
DOIOpen Access PDFOpenAlex
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