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Title: Palladium-catalyzed coupling reaction of allylic diols and cyclic carbonates

Abstract

Pd-catalyzed reaction of organic halides with alkene(Heck-type reaction) is known to be a very convenient method for carbon-carbon bond formation at vinylic positions. Here, the authors report arylation and vinylation of allylic cyclic carbonates and allylic diols. Palladium-catalyzed arylation of allylic cyclic carbonates with iodobenzene afforded phenylsubstituted allylic alcohols via ring opening. However, arylation without ring opening was achieved with diphenyliodonium tetrafluoroborate. The coupling reaction of iodobenzene with allylic diols in the presence of Pd(OAc){sub 2} and nBu{sub 3}P as catalysts afforded the phenyl-substituted allylic diols or phenyl-substituted {alpha}-hydroxy ketones depending on bases used. The mechanism will be discussed. The coupling reaction of hypervalent iodonium salts instead of aryl or vinyl iodide with allylic alcohols provided {beta}-substituted allylic alcohols.

Authors:
; ;  [1]
  1. Sung Kyun Kwan Univ., Suwon (Korea, Republic of); and others
Publication Date:
OSTI Identifier:
250089
Report Number(s):
CONF-9508100-
TRN: 96:002623-0027
Resource Type:
Conference
Resource Relation:
Conference: 8. IUPAC symposium on organometallic chemistry directed towards organic synthesis, Santa Barbara, CA (United States), 6-10 Aug 1995; Other Information: PBD: 1995; Related Information: Is Part Of Eight IUPAC symposium on organometallic chemistry directed towards organic synthesis (OMCOS 8); PB: 375 p.
Country of Publication:
United States
Language:
English
Subject:
40 CHEMISTRY; 10 SYNTHETIC FUELS; ORGANOMETALLIC COMPOUNDS; CATALYTIC EFFECTS; PALLADIUM COMPLEXES; ORGANIC OXYGEN COMPOUNDS; CHEMICAL PREPARATION; CHEMICAL REACTIONS; KETONES; ALCOHOLS

Citation Formats

Kang, Suk-Ku, Jung, Kyung-Yun, and Jang, Su-Bum. Palladium-catalyzed coupling reaction of allylic diols and cyclic carbonates. United States: N. p., 1995. Web.
Kang, Suk-Ku, Jung, Kyung-Yun, & Jang, Su-Bum. Palladium-catalyzed coupling reaction of allylic diols and cyclic carbonates. United States.
Kang, Suk-Ku, Jung, Kyung-Yun, and Jang, Su-Bum. 1995. "Palladium-catalyzed coupling reaction of allylic diols and cyclic carbonates". United States.
@article{osti_250089,
title = {Palladium-catalyzed coupling reaction of allylic diols and cyclic carbonates},
author = {Kang, Suk-Ku and Jung, Kyung-Yun and Jang, Su-Bum},
abstractNote = {Pd-catalyzed reaction of organic halides with alkene(Heck-type reaction) is known to be a very convenient method for carbon-carbon bond formation at vinylic positions. Here, the authors report arylation and vinylation of allylic cyclic carbonates and allylic diols. Palladium-catalyzed arylation of allylic cyclic carbonates with iodobenzene afforded phenylsubstituted allylic alcohols via ring opening. However, arylation without ring opening was achieved with diphenyliodonium tetrafluoroborate. The coupling reaction of iodobenzene with allylic diols in the presence of Pd(OAc){sub 2} and nBu{sub 3}P as catalysts afforded the phenyl-substituted allylic diols or phenyl-substituted {alpha}-hydroxy ketones depending on bases used. The mechanism will be discussed. The coupling reaction of hypervalent iodonium salts instead of aryl or vinyl iodide with allylic alcohols provided {beta}-substituted allylic alcohols.},
doi = {},
url = {https://www.osti.gov/biblio/250089}, journal = {},
number = ,
volume = ,
place = {United States},
year = {Sun Dec 31 00:00:00 EST 1995},
month = {Sun Dec 31 00:00:00 EST 1995}
}

Conference:
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