Boron in Radical Chemistry

Renaud, Philippe

doi:10.1002/9781119953678.rad020

Cited by 17 publications

(14 citation statements)

References 199 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The focus has somewhat shifted in more recent times to tin-free methods [65]. Much progress has been accomplished in the use of organoboranes [66,67] and in transition-metalmediated radical transformations, especially in redox and photoredox reactions [68,69]. Their implication in cascade processes will gain in importance as their use becomes more widespread.…”

Section: Discussionmentioning

confidence: 99%

Some aspects of radical cascade and relay reactions

Quiclet‐Sire¹,

Zard²

2017

Proc. R. Soc. A.

View full text Add to dashboard Cite

The ability to create carbon-carbon bonds is at the heart of organic synthesis. Radical processes are particularly apt at creating such bonds, especially in cascade or relay sequences where more than one bond is formed, allowing for a rapid assembly of complex structures. In the present brief overview, examples taken from the authors' laboratory will serve to illustrate the strategic impact of radical-based approaches on synthetic planning. Transformations involving nitrogen-centred radicals, electron transfer from metallic nickel and the reversible degenerative exchange of xanthates will be presented and discussed. The last method has proved to be a particularly powerful tool for the intermolecular creation of carbon-carbon bonds by radical additions even to unactivated alkenes. Various functional groups can be brought into the same molecule in a convergent manner and made to react together in order to further increase the structural complexity. One important benefit of this chemistry is the so-called RAFT/MADIX technology for the manufacture of block copolymers of almost any desired architecture.

show abstract

Section: Discussionmentioning

confidence: 99%

Some aspects of radical cascade and relay reactions

Quiclet‐Sire¹,

Zard²

2017

Proc. R. Soc. A.

View full text Add to dashboard Cite

show abstract

“…The anionic radical species Ar 3 B •– , which are isoelectronic to the trityl radicals Ar 3 C • , represent the prototypical and earliest class of boron-centered radicals, which were generally obtained by reduction of the corresponding triarylboranes with alkali metals . Recently, numerous neutral radical compounds of the common formula [(NHC)BR 2 ] • , presenting an interest in application as reagents in organic synthesis and efficient co-initiators in various radical polymerization reactions, have been synthesized.…”

Section: Nhc Complexes Of Main Group Elementsmentioning

confidence: 99%

NHCs in Main Group Chemistry

et al. 2018

View full text Add to dashboard Cite

Since the discovery of the first stable N-heterocyclic carbene (NHC) in the beginning of the 1990s, these divalent carbon species have become a common and available class of compounds, which have found numerous applications in academic and industrial research. Their important role as two-electron donor ligands, especially in transition metal chemistry and catalysis, is difficult to overestimate. In the past decade, there has been tremendous research attention given to the chemistry of low-coordinate main group element compounds. Significant progress has been achieved in stabilization and isolation of such species as Lewis acid/base adducts with highly tunable NHC ligands. This has allowed investigation of numerous novel types of compounds with unique electronic structures and opened new opportunities in the rational design of novel organic catalysts and materials. This Review gives a general overview of this research, basic synthetic approaches, key features of NHC-main group element adducts, and might be useful for the broad research community.

show abstract

“…Whilst most of the early studies dealt with the formation of alkyl radicals by autoxidation of trialkylboranes, even at low temperatures, 7 further development spurred by the Renaud group incentive brought to the forefront the utilisation of B-alkylcatecholboranes as radical precursors ( Scheme 1 ). 8 …”

Section: Visible-light-mediated Photogeneration Of Carbon-centred Radmentioning

confidence: 99%