Photoinduced Borylation Reactions: An Overview

Yadagiri, B.; Daipule, Komal; Singh, Surya Prakash

doi:10.1002/ajoc.202000480

Cited by 23 publications

(13 citation statements)

References 111 publications

(187 reference statements)

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“…Only a few reviews have mentioned research progress in this field, and none have covered it in its entirety. ,,− Herein, we systematically and comprehensively summarize research in the field of photoinduced borylation from 1995 to 2020, especially emphasizing recent developments and trends. Different approaches to improve the reactivity and selectivity are analyzed, and their commonalities and differences are addressed.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Borylation for the Synthesis of Organoboron Compounds

et al. 2021

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Organoboron compounds have important synthetic value and can be applied in numerous transformations. The development of practical and convenient ways to synthesize boronate esters has thus attracted significant interest. Photoinduced borylations originated from stoichiometric reactions of alkanes and arenes with well-defined metal–boryl complexes. Now, photoredox-initiated borylations, catalyzed by either transition metal or organic photocatalysts, and photochemical borylations with high efficiency have become a burgeoning area of research. In this Focus Review, we summarize research on photoinduced borylations, especially emphasizing recent developments and trends. This includes the photoinduced borylation of arenes, alkanes, aryl/alkyl halides, activated carboxylic acids, amines, alcohols, and so on based on transition metal catalysis, metal-free organocatalysis, and direct photochemical activation. We focus on reaction mechanisms involving single-electron transfer, triplet-energy transfer, and other radical processes.

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Section: Introductionmentioning

confidence: 99%

Photoinduced Borylation for the Synthesis of Organoboron Compounds

et al. 2021

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“…Organoboron reagents are indispensable tools in the organic chemistry toolbox of synthetic chemists. 1 Organoboron compounds, being the essential synthetic components for carbon-heteroatom and carboncarbon bond making reactions 2,3 provide access to a wide array of valuable and diverse transformations. Their non-toxic nature, excellent functional-group tolerance and diverse reactivity profile are some of the characteristics, which make them unique among the members of the organometallic family, such as organomagnesium or organozinc reagents.…”

Section: Introductionmentioning

confidence: 99%

“…6 The traditional method of electrophilic 2 borylation reaction of aromatic lithium or magnesium reagents derived from aromatic halides with trialkylborates for their synthesis [7][8][9][10] had the major drawback of low functional group compatibility. 2 In contrast, the use of transition-metal catalysts in nucleophilic borylation led to the production of organoboronic esters under mild reaction conditions with higher selectivity and reactivity. Error!…”

Section: Introductionmentioning

confidence: 99%

Nickel-catalyzed (hetero)aryl borylations: an update

Anilkumar¹,

Philip²,

Mole³

2022

Arkivoc

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Aromatic organoboron compounds serve as important intermediates in synthetic organic chemistry. While the traditional electrophilic borylations using aromatic lithium or magnesium reagents had several limitations, transition metal catalyzed borylations emerged as a promising method. In recent years, borylation reactions catalyzed by Ni have gained great attention due to its enormous importance as a cheaper and less toxic alternative to Pd catalysts. The present review focuses on the recent developments in the arena of Ni catalyzed (hetero)aryl borylations after 2013.

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“…Although such progress has been made, the direct and practical C-S bond activation/borylation of aryl sulfides without transition-metal catalysts is highly anticipated. Inspired by the emerging photoinduced radical borylation and aromatic C-S bond cleavage, [30][31][32][33][34][35][36][37][38][39][40] herein we communicate our development of direct C-S bond activation of aryl sulfides via photoinduced aerobic borylation under transition-metal-free conditions (Scheme 1). Remarkably, this C-S borylation was operated simply by combining aryl sulfides, bis( pinacolato)diboron (B 2 pin 2 ), 1,4-benzoquinone, and 1,4-dioxane in a test tube under blue LED illumination and ambient conditions.…”

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confidence: 99%