Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper

Scott C. Berk, Ming-Chang P. Yeh, Nakcheol Jeong, Paul Knochel

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.

Original languageEnglish
Pages (from-to)3053-3064
Number of pages12
JournalOrganometallics
Volume9
Issue number12
DOIs
Publication statusPublished - 1990 Jan 1

Fingerprint

Organometallics
Zinc
Chlorides
Copper
Bearings (structural)
zinc
chlorides
copper
preparation
halides
Dimethyl Sulfoxide
Ketones
Bromides
Aldehydes
Functional groups
Dust
Esters
Salts
aldehydes
ketones

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper. / Berk, Scott C.; Yeh, Ming-Chang P.; Jeong, Nakcheol; Knochel, Paul.

In: Organometallics, Vol. 9, No. 12, 01.01.1990, p. 3053-3064.

Research output: Contribution to journalArticle

Berk, Scott C. ; Yeh, Ming-Chang P. ; Jeong, Nakcheol ; Knochel, Paul. / Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper. In: Organometallics. 1990 ; Vol. 9, No. 12. pp. 3053-3064.
@article{f33d60ded101490c909f4a426128aa10,
title = "Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper",
abstract = "The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10{\%} of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95{\%}) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.",
author = "Berk, {Scott C.} and Yeh, {Ming-Chang P.} and Nakcheol Jeong and Paul Knochel",
year = "1990",
month = "1",
day = "1",
doi = "10.1021/om00162a016",
language = "English",
volume = "9",
pages = "3053--3064",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "12",

}

TY - JOUR

T1 - Preparation and Reactions of Functionalized Benzylic Organometallics of Zinc And Copper

AU - Berk, Scott C.

AU - Yeh, Ming-Chang P.

AU - Jeong, Nakcheol

AU - Knochel, Paul

PY - 1990/1/1

Y1 - 1990/1/1

N2 - The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.

AB - The reaction of zinc dust with primary or secondary benzylic halides 1 bearing various functional groups such as an ester, halide, cyano, or even a ketone group, in THF or, in the case of benzylic chlorides, in THF:DMSO (4:1), furnishes the corresponding zinc organometallics 2 in high yields. The reaction is accompanied by less than 10% of Wurtz coupling products. The benzylic copper organometallics 3, obtained after a transmetalation of 2 with the THF-soluble copper salt CuCN·2LiCl at -20 °C, react in excellent yields (70-95%) with various electrophiles such as acid chlorides, enones, aldehydes, allylic bromides, ethyl propiolate, and tributyltin chloride, leading to the polyfunctional molecules of type 4.

UR - http://www.scopus.com/inward/record.url?scp=0000840453&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000840453&partnerID=8YFLogxK

U2 - 10.1021/om00162a016

DO - 10.1021/om00162a016

M3 - Article

AN - SCOPUS:0000840453

VL - 9

SP - 3053

EP - 3064

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 12

ER -