Isolation and characterization of (Ar)(F)B(OR)2Cs and (PN)CuAr complexes. Involvement of cationic copper(I) species during transmetalation of arylboron reagents with (PN)CuF

Surendra Thapa, Roshan K. Dhungana, Diane A. Dickie, Ramesh Giri

Research output: Contribution to journalArticle

Abstract

We report the synthesis and characterization of novel anionic arylfluoroborate, three-coordinate ligated arylcopper(I) and cationic ligated copper(I) complexes. We show through in situ 19F NMR monitoring that neutral arylboronate ester is more kinetically competent than anionic arylfluoroborate for transmetalation with (PN)CuF (PN = o-(di-tert-butylphosphino)-N,N-dimethylaniline). The transmetalation of the neutral arylboronate ester proceeds via a two-step process involving a cationic copper(I) species wherein an anionic arylfluoroborate is generated in situ as a competent aryl group transferring reagent.

Original languageEnglish (US)
Pages (from-to)4081-4085
Number of pages5
JournalTetrahedron
Volume75
Issue number31
DOIs
StatePublished - Aug 2 2019

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Copper
Esters
Nuclear magnetic resonance
Monitoring
N,N-dimethylaniline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{fb85785f063048548587f835cab67910,
title = "Isolation and characterization of (Ar)(F)B(OR)2Cs and (PN)CuAr complexes. Involvement of cationic copper(I) species during transmetalation of arylboron reagents with (PN)CuF",
abstract = "We report the synthesis and characterization of novel anionic arylfluoroborate, three-coordinate ligated arylcopper(I) and cationic ligated copper(I) complexes. We show through in situ 19F NMR monitoring that neutral arylboronate ester is more kinetically competent than anionic arylfluoroborate for transmetalation with (PN)CuF (PN = o-(di-tert-butylphosphino)-N,N-dimethylaniline). The transmetalation of the neutral arylboronate ester proceeds via a two-step process involving a cationic copper(I) species wherein an anionic arylfluoroborate is generated in situ as a competent aryl group transferring reagent.",
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Isolation and characterization of (Ar)(F)B(OR)2Cs and (PN)CuAr complexes. Involvement of cationic copper(I) species during transmetalation of arylboron reagents with (PN)CuF. / Thapa, Surendra; Dhungana, Roshan K.; Dickie, Diane A.; Giri, Ramesh.

In: Tetrahedron, Vol. 75, No. 31, 02.08.2019, p. 4081-4085.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Isolation and characterization of (Ar)(F)B(OR)2Cs and (PN)CuAr complexes. Involvement of cationic copper(I) species during transmetalation of arylboron reagents with (PN)CuF

AU - Thapa, Surendra

AU - Dhungana, Roshan K.

AU - Dickie, Diane A.

AU - Giri, Ramesh

PY - 2019/8/2

Y1 - 2019/8/2

N2 - We report the synthesis and characterization of novel anionic arylfluoroborate, three-coordinate ligated arylcopper(I) and cationic ligated copper(I) complexes. We show through in situ 19F NMR monitoring that neutral arylboronate ester is more kinetically competent than anionic arylfluoroborate for transmetalation with (PN)CuF (PN = o-(di-tert-butylphosphino)-N,N-dimethylaniline). The transmetalation of the neutral arylboronate ester proceeds via a two-step process involving a cationic copper(I) species wherein an anionic arylfluoroborate is generated in situ as a competent aryl group transferring reagent.

AB - We report the synthesis and characterization of novel anionic arylfluoroborate, three-coordinate ligated arylcopper(I) and cationic ligated copper(I) complexes. We show through in situ 19F NMR monitoring that neutral arylboronate ester is more kinetically competent than anionic arylfluoroborate for transmetalation with (PN)CuF (PN = o-(di-tert-butylphosphino)-N,N-dimethylaniline). The transmetalation of the neutral arylboronate ester proceeds via a two-step process involving a cationic copper(I) species wherein an anionic arylfluoroborate is generated in situ as a competent aryl group transferring reagent.

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