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P-Chiral ferrocenyl phosphines with other substitution patterns on this aromatic ring displayed reduced efficacy (e.g., 2-biphenyl, 28% yield, 18% ee; 2,5-dimethylphenyl, 76% yield, 50% ee; 2-i-Pr-phenyl, 13% yield, 70% ee).
-
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51
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32744468314
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note
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Superior yields were typically obtained in these reactions when conducted in the absence of an additional solvent. However, when solid ketones were employed, toluene was used as a cosolvent.
-
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52
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32744462445
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note
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Ketones containing two alkyl substituents, such as cyclohexyl methyl ketone or cyclopropyl methyl ketone, afforded coupling products in very low yield (< 10%), and α-keto esters were completely ineffective.
-
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53
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-
32744465108
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-
note
-
The yield was improved by conducting this reaction at 35 °C: 55% yield, > 95:5 regioselectivity, 63% ee.
-
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54
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32744474534
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-
note
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Alkynes that lack an alkenyl substituent, such as 1-phenyl-1-propyne or 4-octyne, and 1,3-enynes bearing an aromatic substituent, such as 1-phenyl-3-buten-1-yne, did not undergo coupling under these conditions.
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55
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