1993
DOI: 10.1055/s-1993-22624
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Mg/PbBr2Bimetal Redox-Promoted Stannation of Propargyl, Allyl, Vinyl, and Aryl Halides

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Cited by 26 publications
(11 citation statements)
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“…Our initial studies began with hydrocinnamaldehyde 1 and allenyltributylstannane 2. 5 Treatment of 1 with 2 in the presence of (S)-BINOL-Ti IV (10 mol%) in CH 2 Cl 2 at 220 °C for 24 h afforded only a barely detectable amount of adduct 4. We subsequently observed that synergetic reagents, which were previously utilized for catalytic asymmetric allylation, 6 can also be employed for catalytic asymmetric prop-2-ynylation.…”
mentioning
confidence: 99%
“…Our initial studies began with hydrocinnamaldehyde 1 and allenyltributylstannane 2. 5 Treatment of 1 with 2 in the presence of (S)-BINOL-Ti IV (10 mol%) in CH 2 Cl 2 at 220 °C for 24 h afforded only a barely detectable amount of adduct 4. We subsequently observed that synergetic reagents, which were previously utilized for catalytic asymmetric allylation, 6 can also be employed for catalytic asymmetric prop-2-ynylation.…”
mentioning
confidence: 99%
“…Tin halides (Bu 3 SnCl, Bu 2 SnCl 2 , BuSnCl 3 , SnCl 4 ) were commercially available and were used without any purification. The compounds are commercially available as 1a, 2a, 4a, 2b, 5b, 6b, 1c, 5c, 1d, 2d, 1g, 7g or fully described as 3a [11], 4a [12], 1b [13], 2b [14], 4c [20], 1d [28], 3d [23], 2g [24], 3g [25].…”
mentioning
confidence: 99%
“…Other Rh I catalytic systems were also tested. By changing to a mixture of the cationic complex [Rh(cod) 2 ]BF 4 and the bidentate phosphane binap in CH 2 Cl 2 , conditions typically used with excellent results by Tanaka et al,1g,8 our reaction times were extended to 24 h and the yields of 11 and 13 were worse than those obtained when using the Wilkinson complex (Table 1, Entries 9 and 10 vs. Entries 5 and 7).…”
Section: Resultsmentioning
confidence: 87%