Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates

Lourdes Villar; Joseph P. Bullock; Matheen M. Khan; Arumugam Nagarajan; Roderick W. Bates; Simon G. Bott; Gerardo Zepeda; Francisco Delgado; Joaquin Tamariz

doi:10.1016/0022-328X(96)06112-8

Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates

Lourdes Villar, Joseph P. Bullock, Matheen M. Khan, Arumugam Nagarajan, Roderick W. Bates^*, Simon G. Bott, Gerardo Zepeda, Francisco Delgado, Joaquin Tamariz

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselection. (Ph₃P)₂PdCl₂ also catalyzed cross-coupling alkylation, phenylation and vinylation with trialkylorganostannanes and bromo olefin (Z)-4-bromo-3-(p-nitrobenzoyloxy)-3-buten-2-one (2), providing the corresponding trisubstituted alkenes. For the preparation of n-butyl substituted derivative (Z)-3-(p-nitrobenzoyloxy)-3-octen-2-one (8b), the transmetallation with n-BuZnCl was a more efficient method. Retention of the Z configuration of 2 was in all cases maintained.

Original language	English
Pages (from-to)	9-17
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	517
Issue number	1-2
DOIs	https://doi.org/10.1016/0022-328X(96)06112-8
Publication status	Published - Jun 28 1996
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Keywords

Arylation
Coupling reactions
Olefins
Organostannanes
Palladium
Tin
Zinc

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10.1016/0022-328X(96)06112-8

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title = "Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates",

abstract = "The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselection. (Ph3P)2PdCl2 also catalyzed cross-coupling alkylation, phenylation and vinylation with trialkylorganostannanes and bromo olefin (Z)-4-bromo-3-(p-nitrobenzoyloxy)-3-buten-2-one (2), providing the corresponding trisubstituted alkenes. For the preparation of n-butyl substituted derivative (Z)-3-(p-nitrobenzoyloxy)-3-octen-2-one (8b), the transmetallation with n-BuZnCl was a more efficient method. Retention of the Z configuration of 2 was in all cases maintained.",

keywords = "Arylation, Coupling reactions, Olefins, Organostannanes, Palladium, Tin, Zinc",

author = "Lourdes Villar and Bullock, {Joseph P.} and Khan, {Matheen M.} and Arumugam Nagarajan and Bates, {Roderick W.} and Bott, {Simon G.} and Gerardo Zepeda and Francisco Delgado and Joaquin Tamariz",

year = "1996",

month = jun,

day = "28",

doi = "10.1016/0022-328X(96)06112-8",

language = "English",

volume = "517",

pages = "9--17",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

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T1 - Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates

AU - Villar, Lourdes

AU - Bullock, Joseph P.

AU - Khan, Matheen M.

AU - Nagarajan, Arumugam

AU - Bates, Roderick W.

AU - Bott, Simon G.

AU - Zepeda, Gerardo

AU - Delgado, Francisco

AU - Tamariz, Joaquin

PY - 1996/6/28

Y1 - 1996/6/28

N2 - The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselection. (Ph3P)2PdCl2 also catalyzed cross-coupling alkylation, phenylation and vinylation with trialkylorganostannanes and bromo olefin (Z)-4-bromo-3-(p-nitrobenzoyloxy)-3-buten-2-one (2), providing the corresponding trisubstituted alkenes. For the preparation of n-butyl substituted derivative (Z)-3-(p-nitrobenzoyloxy)-3-octen-2-one (8b), the transmetallation with n-BuZnCl was a more efficient method. Retention of the Z configuration of 2 was in all cases maintained.

AB - The palladium-catalyzed reaction of the captodative olefin 3-(p-nitrobenzoyloxy)-3-buten-2-one (1a) with aryl and vinyl halides gave coupled products 4-aryl-and 4-vinyl-3-(p-nitrobenzoyloxy)-3-buten-2-ones, 4 and 6 respectively, with high Z stereoselection. (Ph3P)2PdCl2 also catalyzed cross-coupling alkylation, phenylation and vinylation with trialkylorganostannanes and bromo olefin (Z)-4-bromo-3-(p-nitrobenzoyloxy)-3-buten-2-one (2), providing the corresponding trisubstituted alkenes. For the preparation of n-butyl substituted derivative (Z)-3-(p-nitrobenzoyloxy)-3-octen-2-one (8b), the transmetallation with n-BuZnCl was a more efficient method. Retention of the Z configuration of 2 was in all cases maintained.

KW - Arylation

KW - Coupling reactions

KW - Olefins

KW - Organostannanes

KW - Palladium

KW - Tin

KW - Zinc

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U2 - 10.1016/0022-328X(96)06112-8

DO - 10.1016/0022-328X(96)06112-8

M3 - Article

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SN - 0022-328X

VL - 517

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EP - 17

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

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ER -

Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates

Abstract

ASJC Scopus Subject Areas

Keywords

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