Back to Search
Start Over
Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B 2 Pin 2 and Isoquinoline.
- Source :
- Molecules; Apr2024, Vol. 29 Issue 8, p1783, 13p
- Publication Year :
- 2024
-
Abstract
- Due to boron's metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple and readily available starting materials still remains a challenge. In this work, we attempted to enhance the reactivity of the electron-donor-acceptor (EDA) complex by selecting different bases to replace the organic base (NEt<subscript>3</subscript>) used in our previous research. To our delight, when using NH<subscript>4</subscript>HCO<subscript>3</subscript> as the base, we have achieved a mild visible-light-mediated aromatic C-H bond borylation reaction with exceptional regioselectivity (rr > 40:1 to single isomers). Compared with our previous borylation methodologies, this protocol provides a more efficient and broader scope for aryl C-H bond borylation through the use of N-Bromosuccinimide. The protocol's good functional-group tolerance and excellent regioselectivity enable the functionalization of a variety of biologically relevant compounds and novel cascade transformations. Mechanistic experiments and theoretical calculations conducted in this study have indicated that, for certain arenes, the aryl C-H bond borylation might proceed through a new reaction mechanism, which involves the formation of a novel transient EDA complex. [ABSTRACT FROM AUTHOR]
- Subjects :
- BORYLATION
ORGANIC bases
BORON compounds
AROMATIC compounds
ISOMERS
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 29
- Issue :
- 8
- Database :
- Complementary Index
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- 176904808
- Full Text :
- https://doi.org/10.3390/molecules29081783