Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Giustra, Zachary X; Yang, Xinyu; Chen, Min; Bettinger, Holger F; Liu, Shih-Yuan

Giustra, Zachary X; Yang, Xinyu; Chen, Min; Bettinger, Holger F; Liu, Shih-Yuan.

Afiliação

Giustra ZX; Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.
Yang X; Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.
Chen M; Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.
Bettinger HF; Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076, Tübingen, Germany.
Liu SY; Department of Chemistry, Boston College, Chestnut Hill, MA, 02467-3860, USA.

Angew Chem Int Ed Engl ; 58(52): 18918-18922, 2019 12 19.

Article em En | MEDLINE | ID: mdl-31604006

ABSTRACT

ABSTRACT

We provide a seminal example of the utility of the 1,2-azaborine motif as a 4C+1N+1B synthon in organic synthesis. Specifically, conditions for the practically scalable photoisomerization of 1,2-azaborine in a flow reactor are reported that furnish aminoborylated cyclobutane derivatives. The C-B bonds could also be functionalized to furnish a diverse set of highly substituted cyclobutanes.

Assuntos

Compostos Aza/química; Compostos de Boro/química; Ciclobutanos/química

Palavras-chave

boron-nitrogen heterocycles; flow chemistry; photochemistry; small ring systems; valence isomerization

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Compostos Aza / Compostos de Boro / Ciclobutanos Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Estados Unidos

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