Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides

Dmitri Gelman; Lei Jiang; Stephen L. Buchwald

doi:10.1021/ol0346640

Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides

Dmitri Gelman, Lei Jiang, Stephen L. Buchwald^*

^*Corresponding author for this work

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

291 Scopus citations

Abstract

(Matrix presented) A general method for the coupling of aryl and vinyl halides with diaryl and dialkyl phosphines, as well as with dibutyl phosphite, is reported. This highly efficient transformation is realized through the use of copper(I) iodide as a catalyst, N,N′-dimethylethylenediamine as a ligand, and Cs₂CO₃ as a base. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.

Original language	English
Pages (from-to)	2315-2318
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	13
DOIs	https://doi.org/10.1021/ol0346640
State	Published - 26 Jun 2003
Externally published	Yes

Access to Document

10.1021/ol0346640

Cite this

@article{f7caed5834fe4e8ead0a654073a60186,

title = "Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides",

abstract = "(Matrix presented) A general method for the coupling of aryl and vinyl halides with diaryl and dialkyl phosphines, as well as with dibutyl phosphite, is reported. This highly efficient transformation is realized through the use of copper(I) iodide as a catalyst, N,N′-dimethylethylenediamine as a ligand, and Cs2CO3 as a base. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.",

author = "Dmitri Gelman and Lei Jiang and Buchwald, {Stephen L.}",

year = "2003",

month = jun,

day = "26",

doi = "10.1021/ol0346640",

language = "אנגלית",

volume = "5",

pages = "2315--2318",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides

AU - Gelman, Dmitri

AU - Jiang, Lei

AU - Buchwald, Stephen L.

PY - 2003/6/26

Y1 - 2003/6/26

N2 - (Matrix presented) A general method for the coupling of aryl and vinyl halides with diaryl and dialkyl phosphines, as well as with dibutyl phosphite, is reported. This highly efficient transformation is realized through the use of copper(I) iodide as a catalyst, N,N′-dimethylethylenediamine as a ligand, and Cs2CO3 as a base. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.

AB - (Matrix presented) A general method for the coupling of aryl and vinyl halides with diaryl and dialkyl phosphines, as well as with dibutyl phosphite, is reported. This highly efficient transformation is realized through the use of copper(I) iodide as a catalyst, N,N′-dimethylethylenediamine as a ligand, and Cs2CO3 as a base. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.

UR - http://www.scopus.com/inward/record.url?scp=0141741556&partnerID=8YFLogxK

U2 - 10.1021/ol0346640

DO - 10.1021/ol0346640

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 12816437

AN - SCOPUS:0141741556

SN - 1523-7060

VL - 5

SP - 2315

EP - 2318

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides

Abstract

Access to Document

Other files and links

Fingerprint

Cite this