New avenues for C–B bond formation<i>via</i>radical intermediates

Friese, Florian W.; Studer, Armido

doi:10.1039/c9sc03765a

Cited by 131 publications

(54 citation statements)

References 130 publications

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“…In recent years, radical chemistry has experienced a renaissance and accordingly also boron‐based radical chemistry has matured. Various methods for C‐radical borylation to access boronic esters have been developed . In these reactions, the boron moiety gets introduced into an organic compound.…”

Section: Discussionmentioning

confidence: 99%

Radical‐Induced 1,2‐Migrations of Boron Ate Complexes

2020

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Section: Discussionmentioning

confidence: 99%

Radical‐Induced 1,2‐Migrations of Boron Ate Complexes

2020

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“…Organoboron compounds have been recognized as extremely useful and readily accessible synthetic intermediates in organic synthesis for many decades -from Nobelprize-winning works of Brown on organoboranes, 1,2 to palladium-catalyzed reaction of boronic acids developed by Suzuki (also awarded with the Nobel prize) 3,4 and more recent discoveries like Chan-Lam 5 and radical photoredox couplings of trifluoroborates. 6 Much attention has been given to the increasing utility of organoboron compounds as building blocks in the construction of complex molecules (for recent general reviews, see [7][8][9][10] ). Recently, renewed interest in organic boron-containing molecules is related to their direct biological and medicinal applications, in particular, for the design of covalent inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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“…Reactions involving boryl radicals as key intermediates have been found to proceed via distinct mechanisms,enabling pertinent molecular transformations. [3,4] In particular, N-heterocyclic carbene (NHC)-boryl radicals have emerged as ac lass of powerful reactive species to enable various significant syntheses [5] and catalysis. [6] In this context, Curran, Taniguchi, and Walton, [7] as well as our research group, [8] have independently developed as eries of radical borylation reactions with alkenes and alkynes for the synthesis of organoboron molecules (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

New Radical Borylation Pathways for Organoboron Synthesis Enabled by Photoredox Catalysis

Zhang

Jin

et al. 2020

Angewandte Chemie

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Radical borylation using N‐heterocyclic carbene (NHC)‐BH3 complexes as boryl radical precursors has emerged as an important synthetic tool for organoboron assembly. However, the majority of reported methods are limited to reaction modes involving carbo‐ and/or hydroboration of specific alkenes and alkynes. Moreover, the generation of NHC‐boryl radicals relies principally on hydrogen atom abstraction with the aid of radical initiators. A distinct radical generation method is reported, as well as the reaction pathways of NHC‐boryl radicals enabled by photoredox catalysis. NHC‐boryl radicals are generated via a single‐electron oxidation and subsequently undergo cross‐coupling with the in‐situ‐generated radical anions to yield gem‐difluoroallylboronates. A photoredox‐catalyzed radical arylboration reaction of alkenes was achieved using cyanoarenes as arylating components from which elaborated organoborons were accessed. Mechanistic studies verified the oxidative formation of NHC‐boryl radicals through a single‐electron‐transfer pathway.

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New avenues for C–B bond formationviaradical intermediates

Abstract: Efficient radical routes to important alkyl and aryl boronic esters have been developed over the past few years. Such reactions are complementary to existing transition-metal catalysed cross coupling processes.

Cited by 131 publications

References 130 publications

Radical‐Induced 1,2‐Migrations of Boron Ate Complexes

Radical‐Induced 1,2‐Migrations of Boron Ate Complexes

Cycloadditions of Alkenylboronic Derivatives

New Radical Borylation Pathways for Organoboron Synthesis Enabled by Photoredox Catalysis

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