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Synthesis 2017; 49(11): 2411-2422
DOI: 10.1055/s-0036-1588705
DOI: 10.1055/s-0036-1588705
paper
Pd(OAc)2-Catalyzed Desulfinative Cross-Coupling of Sodium Sulfinates with β-Bromostyrenes: Synthesis of Tamoxifen
Further Information
Publication History
Received: 29 December 2016
Accepted after revision: 17 January 2017
Publication Date:
07 February 2017 (online)

Abstract
A Pd(OAc)2-catalyzed desulfinative cross-coupling of (Z)-β-halostyrenes with sodium sulfinates in the presence of PPh3 and Na2CO3 at reflux in good yields is reported. The stereocontrolled cross-coupling process provides a series of sulfonylmethyl (Z)-stilbenes. A synthesis of tamoxifen was studied.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588705. Scanned photocopies
of NMR (CDCl3) spectral data for all compounds and X-ray crystal structure analysis data of 6n, 6s, 7c, 7g
and 8a are included.
- Supporting Information
- CIF File
-
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For selected examples on Julia–Kocienski olefination, see:
For selected examples on the Horner–Wadsworth–Emmons reaction, see:
For selected examples on the Ramberg–Backlund rearrangement, see:
For selected examples on the McMurry coupling, see:
For Pd2+-mediated cross-coupling of styrenes, see:
For Rh3+-mediated cross-coupling of styrenes, see:
For isomerization of stilbenes, see:
Desulfinative route toward the synthesis of stilbenes with Pd2+: For ArSO2H/styrenes, see:
For ArSO2NHNH2/styrenes, see:
For ArSO2Na/styrenes, see:
For reviews on desulfinative cross-coupling, see:
Selected examples on the desulfinative carbonylation of carbonyl synthons, for nitriles/Pd2+, see:
For aldehydes/Rh+, see:
For examples on desulfinative conjugation of enones, see:
For examples on direct desulfinative arylation of heterocycles with Pd2+: For indoles, see:
For thiazoles, benzoxazoles, and benzothiazoles, see:
For oxazoles, thiazoles, and 1,3,4-oxadiazoles, see:
For benzothiophenes and thiophenes, see:
For coumarins, see:
For furans, see:
For benzo[d]oxazoles, see:
For benzofurans, see:
For lactones, see:
Examples on biological activities of the core structures with the sulfonylmethyl motif, for styrenes, see:
For pyrimidines, see:
For tryptamines, see:
For chalcones, see:
Desulfinative homocoupling of arylsulfinates with Pd2+, see:
Metal-catalyzed self-dimerization of β-bromostyrenes, for Ni2+, see:
For Cr3+, see:
For Pd2+, see:
For Au3+, see:
For Co2+, see: