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

doi:10.1016/j.tet.2019.05.071

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	4081-4085
Number of pages	5
Journal	Tetrahedron
Volume	75
Issue number	31
DOIs	https://doi.org/10.1016/j.tet.2019.05.071
State	Published - Aug 2 2019

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2019.05.071

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.",

author = "Surendra Thapa and Dhungana, {Roshan K.} and Dickie, {Diane A.} and Ramesh Giri",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = aug,

day = "2",

doi = "10.1016/j.tet.2019.05.071",

language = "English (US)",

volume = "75",

pages = "4081--4085",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "31",

}

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.

UR - http://www.scopus.com/inward/record.url?scp=85066458077&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85066458077&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2019.05.071

DO - 10.1016/j.tet.2019.05.071

M3 - Article

AN - SCOPUS:85066458077

SN - 0040-4020

VL - 75

SP - 4081

EP - 4085

JO - Tetrahedron

JF - Tetrahedron

IS - 31

ER -

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

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this