Selective α-Stannylated Addition of Di-<i>n</i>-butyliodotin Hydride Ate Complex to Simple Aliphatic Alkynes

Shibata, Ikuya; Suwa, Toshihiro; Ryu, Kyoichiro; Baba, Akio

doi:10.1021/ja0056973

Cited by 44 publications

(21 citation statements)

References 5 publications

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“…98 Halide ions can similarly be added to give complexes such as Bu 2 SnHClF -Bu 4 N + , Bu 2 SnHBrI -MgBr + , and Bu 2 SnHI 2 -Li + . 99,100 . Again, the halide ions are assumed to occupy the apical positions in a trigonal bipyramid.…”

Section: S Nhmentioning

confidence: 99%

Recent Advances in the Chemistry of the Organotin Hydrides

Davies

2006

Journal of Chemical Research

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Section: S Nhmentioning

confidence: 99%

Recent Advances in the Chemistry of the Organotin Hydrides

Davies

2006

Journal of Chemical Research

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“…40 The use of 2 equiv of MgBr 2 OEt 2 , 0.5 equiv of 29a and the employment of EtOAc as a solvent sharply increased the yield of 30a up to 86%. The sole use of iodotin hydride, Bu 2 SnlH, gave a mixture of 31a-E and 31a-Z.…”

Section: Scheme 16mentioning

confidence: 99%

Synthetic Applications of a Series of Organotin Hydrides

Ikuya¹,

Suwa²,

Baba³

2001

Main Group Metal Chemistry

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“…To date, reports of the hydrostannation of VCPs have been rare 14. Our group has developed a di‐ n ‐butyliodotin hydride (Bu 2 SnIH)‐promoted hydrostannation of alkynes,15a allenes,15b and methylene cyclopropanes15c involving radical chain reactions and the formation of various vinylic tin compounds. Herein, we report the hydrostannation of VCPs by using Bu 2 SnIH, which forms allyltins 2 , and a successive one‐pot coupling with aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Transition‐Metal‐Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride

Ieki

Kani

Tsunoi

et al. 2015

Chemistry A European J

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Donor-acceptor cyclopropanes are useful building blocks for catalytic cycloaddition reactions with a range of electrophiles to give various cyclic products. In contrast, relatively few methods are available for the synthesis of homoallylic alcohols through coupling of vinylcyclopropanes (VCPs) with aldehydes, even with transition-metal catalysts. Here, we report that the hydrostannation of vinylcyclopropanes (VCPs) was effectively promoted by dibutyliodotin hydride (Bu2 SnIH). The resultant allylic tin compounds reacted easily with aldehydes. Furthermore, the use of Bu2 SnIH was effectively catalytic in the presence of hydrosilane as a hydride source, which established a coupling reaction of VCPs with aldehydes for the synthesis of homoallylic alcohols without the use of transition-metal catalysts. In contrast to conventional catalytic reactions of VCPs, the presented method allowed the use of several VCPs in addition to conventional donor-acceptor cyclopropanes.

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Selective α-Stannylated Addition of Di-n-butyliodotin Hydride Ate Complex to Simple Aliphatic Alkynes

Cited by 44 publications

References 5 publications

Recent Advances in the Chemistry of the Organotin Hydrides

Recent Advances in the Chemistry of the Organotin Hydrides

Synthetic Applications of a Series of Organotin Hydrides

Transition‐Metal‐Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride

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