Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9‐BBN‐Derived Ate Complexes

Law, Chunyin; Meng, Yu; Koo, S.; Morken, James P.

doi:10.1002/ange.201901927

Angewandte Chemie

2019

DOI: 10.1002/ange.201901927

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Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9‐BBN‐Derived Ate Complexes

Chunyin Law

Yu Meng

S. Koo

et al.

Abstract: b-Boryl carbonyl compounds are produced by aNicatalyzedc ross-coupling of vinylboron "ate" complexes and acid chloride or acid anhydride electrophiles.The reactions are efficient, being complete in as little as two minutes,and can be applied to abroad range of substrates.

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Cited by 19 publications

References 68 publications

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An Olefinic 1,2‐Boryl‐Migration Enabled by Radical Addition: Construction ofgem‐Bis(boryl)alkanes

Zhao

et al. 2019

Angewandte Chemie

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As eries of in situ formed alkenyl diboronate complexes from alkenyl Grignard reagents (commercially available or prepared from alkenyl bromides and Mg) with B 2 Pin 2 (bis(pinacolato)diboron) react with diverse alkyl halides by aR up hotocatalyst to give various gem-bis-(boryl)alkanes.A lkyl radicals add efficiently to the alkenyl diboronate complexes,and the adduct radical anions undergo radical-polar crossover,s pecifically,a1,2-boryl-anion shift from boron to the a-carbon sp 2 center.T his transformation shows good functional-group compatibility and can serve as ap owerful synthetic tool for late-stage functionalization in complex compounds.M easurements of the quantum yield reveal that aradical-chain mechanism is operative in whichthe alkenyl diboronates acts as reductive quencher for the excited state of the photocatalyst.

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An Olefinic 1,2‐Boryl‐Migration Enabled by Radical Addition: Construction ofgem‐Bis(boryl)alkanes

Zhao

et al. 2019

Angewandte Chemie

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Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

Chierchia

Lovinger

et al. 2019

Angewandte Chemie

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Site‐Selective 1,2‐Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

et al. 2020

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Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9‐BBN‐Derived Ate Complexes

Abstract: b-Boryl carbonyl compounds are produced by aNicatalyzedc ross-coupling of vinylboron "ate" complexes and acid chloride or acid anhydride electrophiles.The reactions are efficient, being complete in as little as two minutes,and can be applied to abroad range of substrates.

Cited by 19 publications

References 68 publications

An Olefinic 1,2‐Boryl‐Migration Enabled by Radical Addition: Construction ofgem‐Bis(boryl)alkanes

An Olefinic 1,2‐Boryl‐Migration Enabled by Radical Addition: Construction ofgem‐Bis(boryl)alkanes

Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

Site‐Selective 1,2‐Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

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