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Sterically Unprotected Nucleophilic Boron Cluster Reagents.

ABSTRACT: A cornerstone of modern synthetic chemistry rests on the ability to manipulate the reactivity of a carbon center by rendering it either electrophilic or nucleophilic. However, accessing a similar reactivity spectrum with boron-based reagents has been significantly more challenging. While classical nucleophilic carbon-based reagents normally do not require steric protection, readily accessible, unprotected boron-based nucleophiles have not yet been realized. Herein, we demonstrate that the bench stable closo-hexaborate cluster anion can engage in a nucleophilic substitution reaction with a wide array of organic and main group electrophiles. The resulting molecules containing B?C bonds can be further converted to tricoordinate boron species widely used in organic synthesis.

SUBMITTER: Mu X

PROVIDER: S-EPMC7156033 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Sterically Unprotected Nucleophilic Boron Cluster Reagents.

Mu Xin X Axtell Jonathan C JC Bernier Nicholas A NA Kirlikovali Kent O KO Jung Dahee D Umanzor Alexander A Qian Kevin K Chen Xiangyang X Bay Katherine L KL Kirollos Monica M Rheingold Arnold L AL Houk K N KN Spokoyny Alexander M AM

Chem 20190822 9

A cornerstone of modern synthetic chemistry rests on the ability to manipulate the reactivity of a carbon center by rendering it either electrophilic or nucleophilic. However, accessing a similar reactivity spectrum with boron-based reagents has been significantly more challenging. While classical nucleophilic carbon-based reagents normally do not require steric protection, readily accessible, unprotected boron-based nucleophiles have not yet been realized. Herein, we demonstrate that the bench ...[more]

PMID: 32292833

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