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Synthesis 2022; 54(09): 2157-2164
DOI: 10.1055/a-1730-2473
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Tuning StackPhim Ligands: Applications in Enantioselective Borylation and Alkynylation

Gaurav Dahiya 
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
,
Khalil A. Abboud
b   Center for X-ray Crystallography, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
,
Aaron Aponick  ∗
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
› Author AffiliationsThe authors thank the University of Florida and the National Science Foundation (CHE-1900299) for their generous support. Mass spectrometry instrumentation was supported by a grant from the National Institutes of Health (S10 OD021758-01A1).
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Abstract

Here we present a new stack ligand with a modified imidazoline backbone prepared from cyclohexanediamine. This new stack ligand­, Cy-StackPhim, has been found to complement the parent StackPhim ligand in an enantioselective borylation reaction. Additionally, a correlation between the nature of substituents on the imidazoline ring and the substituents on the electrophile is also discussed.

Key words

axial chirality - stack ligands - P,N-ligands - ligand tuning - borylation­ - alkynylation - A3-coupling - ligand synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1730-2473.
  • Supporting Information


Publication History

Received: 24 November 2021

Accepted after revision: 03 January 2022

Accepted Manuscript online:
03 January 2022

Article published online:
23 March 2022

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