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Literature DB >> 23981246

Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes.

Xiangcheng Pan¹, Anne Boussonnière, Dennis P Curran.

Abstract

The hydroboration of alkenes of diverse structural types by assorted N-heterocyclic carbene boranes can be accomplished by addition of 5-10% diiodine. For example, reaction of 1,3-dimethylimidazol-2-ylidene borane (diMe-Imd-BH3) with 10% I2 followed by addition of 2,3-dimethyl-2-butene provided the corresponding thexyl NHC-borane (diMe-Imd-BH2thexyl) in 75% yield. This and related monohydroboration products are stable to chromatography and storage. The scope of the new reaction is described, and the mechanism is probed by (11)B NMR experiments.

Entities: Chemical Disease

Year: 2013 PMID： 23981246 DOI： 10.1021/ja407678e

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

4 in total

4. Reductive α-borylation of α,β-unsaturated esters using NHC-BH₃ activated by I₂ as a metal-free route to α-boryl esters.

Authors: James E Radcliffe; Valerio Fasano; Ralph W Adams; Peiran You; Michael J Ingleson
Journal: Chem Sci Date: 2018-11-19 Impact factor: 9.825

4 in total

Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes.

1. Using Ylide Functionalization to Stabilize Boron Cations.

2. N-Heterocycle-Ligated Borocations as Highly Tunable Carbon Lewis Acids.

3. A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.

4. Reductive α-borylation of α,β-unsaturated esters using NHC-BH₃ activated by I₂ as a metal-free route to α-boryl esters.

Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes.

1. Using Ylide Functionalization to Stabilize Boron Cations.

2. N-Heterocycle-Ligated Borocations as Highly Tunable Carbon Lewis Acids.

3. A family of N-heterocyclic carbene-stabilized borenium ions for metal-free imine hydrogenation catalysis.

4. Reductive α-borylation of α,β-unsaturated esters using NHC-BH3 activated by I2 as a metal-free route to α-boryl esters.

4. Reductive α-borylation of α,β-unsaturated esters using NHC-BH₃ activated by I₂ as a metal-free route to α-boryl esters.