Work

Reductive coupling of azonaphthalenes for the synthesis of BINAMs via a diboron-enabled [5,5]-sigmatropic rearrangement

Year: 2024

Type: article

Abstract: The [5,5]-sigmatropic rearrangement is a less-studied reaction and may be strategically utilized to devise unique synthetic processes. Herein, we document a diboron-enabled [5,5]-sigmatropic rearrangement for practical synthesis of BINAM derivatives. Mechanistically, a concerted activation of azonaphthalenes by diboron creates a unique ten-membered transition state, which subsequently triggers a [5,5]-sigmatropic rearrangement. The reaction occurs under mild conditions, and offers operational simplicity, remarkable chemo- and regioselectivities, and good scalability (>10 grams).

Source: Chemical Science

DOI: 10.1039/d4sc06273f

Authors: Liang-Wen Qi, Emmanuella Bema Twumasi, Xiao-Wei Li, Rui Li, Yixin Lu

Institution: National University of Singapore

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National University of Singapore, Ministry of Education - Singapore, Ministry of Education, India

Awards: G5311639528, G7503138121