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Radical-Polar Crossover Reactions of Dienylboronate Complexes: Synthesis of Functionalized Allylboronic Esters.

ABSTRACT: Radical-polar crossover reactions of dienylboronate complexes are applied to the synthesis of functionalized secondary and tertiary allylboronic esters. The transition-metal-free three-component coupling uses readily accessible dienylboronate esters as substrates in combination with various sp3/sp2 carbon nucleophiles and commercial alkyl iodides as radical precursors. In the visible light-initiated radical chain process, two new C-C bonds are formed, and the E-double bond geometry in the product allylboronic esters is controlled with good to excellent selectivity.

SUBMITTER: Kischkewitz M

PROVIDER: S-EPMC6039077 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Radical-Polar Crossover Reactions of Dienylboronate Complexes: Synthesis of Functionalized Allylboronic Esters.

Kischkewitz Marvin M Gerleve Carolin C Studer Armido A

Organic letters 20180606 12

Radical-polar crossover reactions of dienylboronate complexes are applied to the synthesis of functionalized secondary and tertiary allylboronic esters. The transition-metal-free three-component coupling uses readily accessible dienylboronate esters as substrates in combination with various sp<sup>3</sup>/sp<sup>2</sup> carbon nucleophiles and commercial alkyl iodides as radical precursors. In the visible light-initiated radical chain process, two new C-C bonds are formed, and the E-double bond ...[more]

PMID: 29874093

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