Phosphine‐Catalyzed <i>anti</i>‐Carboboration of Alkynoates with 9‐BBN‐Based 1,1‐Diborylalkanes: Synthesis and Use of Multisubstituted γ‐Borylallylboranes

Over the past few decades, organophosphorus catalysis has emerged as a robust platform for the preparation of highly functionalized molecules with excellent control of reactivity and selectivity. Organophosphorus catalysis has the advantages of mild and metal‐free reaction conditions. The easy‐to‐tune electronic and steric properties of phosphorus provide an easy handle for developing efficient synthetic methodologies with high stereochemical fidelity. This review describes the efforts to introduce boron and silicon functionalities into organic substrates catalyzed by organophosphorus compounds. These catalysts are categorized into nucleophilic, electrophilic, and biphilic phosphorus catalysts. Phosphorus compounds efficiently catalyze hydroboration of various unsaturated systems, carbonyl compounds, imines, etc.; hydro‐/cyano‐silylation of carbonyls; and silylation of alcohols. The present review emphasizes the scope of nucleophilic, electrophilic, and biphilic phosphorus‐based catalysis to introduce boron and silicon functionalities into organic compounds, mainly from the recent decade.

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Recent Advances in Organophosphorus‐Catalyzed Borylation and Silylation Reactions

Biswas

Das

Ganesh

2021

Adv Synth Catal

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Chemoselective Palladium‐Catalyzed Suzuki‐Miyaura Cross‐Coupling of (Diborylmethyl)silanes with Alkenyl Bromides

2019

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Herein, we report the development of a palladium‐catalyzed chemoselective cross‐coupling of (diborylmethyl)silanes with alkenyl bromides. The reaction shows broad scope with respect to alkenyl bromides and (diborylmethyl)silanes, affording a range of α‐silyl‐substituted allylic boronate esters in good‐to‐excellent yields. The practicality of the developed coupling reaction is demonstrated by the gram‐scale synthesis of α‐silyl‐substituted allylic boronate ester.

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Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem‐Diborylalkanes by an Asymmetric Allylic Substitution

2018

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We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X = Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing as tereogenic center at the bposition of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has ab road substrate scope,a nd various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to ad iverse set of valuable chiral building blocks.Scheme 1. Use of gem-diborylalkanes. pin = pinacol.

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Phosphine‐Catalyzed anti‐Carboboration of Alkynoates with 9‐BBN‐Based 1,1‐Diborylalkanes: Synthesis and Use of Multisubstituted γ‐Borylallylboranes

Cited by 15 publications

References 54 publications

Recent Advances in Organophosphorus‐Catalyzed Borylation and Silylation Reactions

Recent Advances in Organophosphorus‐Catalyzed Borylation and Silylation Reactions

Chemoselective Palladium‐Catalyzed Suzuki‐Miyaura Cross‐Coupling of (Diborylmethyl)silanes with Alkenyl Bromides

Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem‐Diborylalkanes by an Asymmetric Allylic Substitution

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