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

Research output: Contribution to journalArticle

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 languageAmerican English
Pages (from-to)9-17
Number of pages7
JournalJournal of Organometallic Chemistry
DOIs
StatePublished - 28 Jun 1996

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Palladium
Alkenes
alkenes
Olefins
palladium
cross coupling
alkylation
Alkylation
halides
Derivatives
preparation
products
configurations
3-buten-2-one

Cite this

Villar, Lourdes ; Bullock, Joseph P. ; Khan, Matheen M. ; Nagarajan, Arumugam ; Bates, Roderick W. ; Bott, Simon G. ; Zepeda, Gerardo ; Delgado, Francisco ; Tamariz, Joaquin. / Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates. In: Journal of Organometallic Chemistry. 1996 ; pp. 9-17.
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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.",
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Highly stereoselective palladium-catalyzed coupling reactions of captodative olefins acetylvinyl arenecarboxylates. / Villar, Lourdes; Bullock, Joseph P.; Khan, Matheen M.; Nagarajan, Arumugam; Bates, Roderick W.; Bott, Simon G.; Zepeda, Gerardo; Delgado, Francisco; Tamariz, Joaquin.

In: Journal of Organometallic Chemistry, 28.06.1996, p. 9-17.

Research output: Contribution to journalArticle

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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.

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