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Palladium-catalyzed Homogeneous Coupling Reactions of Steroids With Organostannanes

Palladium-catalyzed Homogeneous Coupling Reactions of Steroids With Organostannanes

R Skoda-Földes, Z Csákai, L Kollár, J Horváth, Z Tuba

Steroids. 1995 Dec;60(12):812-6.

PMID: 8650704

Abstract:

Direct and carbonylative coupling reactions of various steroid derivatives possessing iodo- and bromo-alkenyl moiety (17-iodo-androst-16-ene, 1, 17-bromoandrost-2,16-diene, 2, 17-iodo-4-aza-4-methylandrost-16-en-3-one, 3, 17-iodo-4-azaandrost-16-en-3-one, 4) with vinyltributylstannane and ethynyltributylstannane were carried out in the presence of various palladium catalysts. While carbonylation took place only with vinyltributylstannane, 17-vinyl-, and 17-ethynyl-delta 16 steroids were produced via direct coupling with vinyltributylstannane and ethynyltributylstannane, respectively. Activities of some catalysts based on Pd(0) and Pd(II) precursors were compared, and Pd(PPh3)4 was found to be superior to other complexes in most cases. In the coupling of 17-iodoandrost-16-ene with organostannanes Pd2(dba)3 + 8 AsPh3 in situ catalyst was found to be even more effective.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP994898	Ethynyltributylstannane		994-89-8	Price

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