Visible‐Light‐Promoted Photocatalytic B−C Coupling via a Boron‐Centered Carboranyl Radical: Facile Synthesis of B(3)‐Arylated  o ‐Carboranes | Zendy

Zhao Da | Zendy; Xie Zuowei | Zendy

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Visible‐Light‐Promoted Photocatalytic B−C Coupling via a Boron‐Centered Carboranyl Radical: Facile Synthesis of B(3)‐Arylated o ‐Carboranes

Author(s) -

Zhao Da,

Xie Zuowei

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201511251

Subject(s) - eosin y , boron , tetrafluoroborate , chemistry , carborane , electrophilic substitution , photocatalysis , visible spectrum , electrophile , photochemistry , catalysis , electrophilic aromatic substitution , medicinal chemistry , organic chemistry , materials science , ionic liquid , optoelectronics

A visible‐light‐mediated in situ generation of a boron‐centered carboranyl radical ( o ‐C 2 B 10 H 11 . ) has been described. With eosin Y as a photoredox catalyst, 3‐diazonium‐ o ‐carborane tetrafluoroborate [3‐N 2 ‐ o ‐C 2 B 10 H 11 ][BF 4 ] was converted into the corresponding boron‐centered carboranyl radical intermediate, which can undergo efficient electrophilic substitution reaction with a wide range of (hetero)arenes. This general and simple procedure provides a metal‐free alternative for the synthesis of 3‐(hetero)arylated‐ o ‐carboranes.

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