Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides

Gary A. Molander; Inji Shin; Ludivine Jean-Gérard

doi:10.1021/ol101865e

Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides

Gary A. Molander, Inji Shin, Ludivine Jean-Gérard

Dept. of Fine Chemistry

University of Pennsylvania

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

25 Scopus citations

Abstract

Figure Presented. Enantiomerically enriched potassium β- trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.

Original language	English
Pages (from-to)	4384-4387
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	19
DOIs	https://doi.org/10.1021/ol101865e
State	Published - 1 Oct 2010

Access to Document

10.1021/ol101865e

Cite this

@article{33151f8a38ba44339c5b36b2222d8ab7,

title = "Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides",

abstract = "Figure Presented. Enantiomerically enriched potassium β- trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.",

author = "Molander, \{Gary A.\} and Inji Shin and Ludivine Jean-G{\'e}rard",

year = "2010",

month = oct,

day = "1",

doi = "10.1021/ol101865e",

language = "English",

volume = "12",

pages = "4384--4387",

journal = "Organic Letters",

issn = "1523-7060",

number = "19",

}

TY - JOUR

T1 - Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides

AU - Molander, Gary A.

AU - Shin, Inji

AU - Jean-Gérard, Ludivine

PY - 2010/10/1

Y1 - 2010/10/1

N2 - Figure Presented. Enantiomerically enriched potassium β- trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.

AB - Figure Presented. Enantiomerically enriched potassium β- trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.

UR - http://www.scopus.com/inward/record.url?scp=77957115642&partnerID=8YFLogxK

U2 - 10.1021/ol101865e

DO - 10.1021/ol101865e

M3 - Article

C2 - 20831191

AN - SCOPUS:77957115642

SN - 1523-7060

VL - 12

SP - 4384

EP - 4387

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides

Abstract

Access to Document

Other files and links

Fingerprint

Cite this