Cu(I)-Catalyzed Regioselective Synthesis of Substituted Allyl Furans and Thiophenes Using Organostannanes

Abstract

2-Allyl-substituted furans and thiophenes were efficiently synthesized from organostannyl derivatives as starting materials using Cu(I) as catalyst. The effect of DMF and NMP as solvents are discussed, as well as other solvent and temperature effects.

Conjugate additions of furylcuprates to α-enones. The effect of the copper precursor and of TMSCl used as additive

“…CuBr was prepared similarly to the way described for CuCl. 26 All glassware, syringes, and needles were dried in an oven at 130 ºC overnight and cooled in a desiccator.…”

C−C Coupling between an η3-Allyl Ligand and Carbon Nucleophiles in Molybdenum and Tungsten Complexes: Structural Characterization of the Key Intermediate

“…Similar reactions were conducted with Li (alkyl) or K (enolate) reagents to give the products indicated in Scheme . Available data for the trans ‐dicarbonyl complexes, reaction times, and references for the non‐commercial coupling products are given: 11: IR: $\tilde \nu$ =1841 s cm −1 , 2 h; 12 : commercial; 13 : $\tilde \nu$ =1840 s cm −1 , 31 P{ 1 H} NMR (CDCl 3 ): δ =−4.72, −18.79 (ABq, 2 J (P,P)=69.5 Hz), 30 min; 14 :16; 15 : $\tilde \nu$ =1845 s cm −1 , 40 min; 16: 17; 17 : $\tilde \nu$ =1840 s, 1689 s cm −1 , 31 P{ 1 H} NMR (CDCl 3 ): δ =67.27, 11.73 (ABq, 2 J (P,P)=26.8 Hz), 2 h; 18 :18; 19 : $\tilde \nu$ =1847 s, 1784 s cm −1 , 4 h; 20 :19; 21 : $\tilde \nu$ =1843 s, 1785 s cm −1 , 4 h; 22 : commercial. Experimental details for 2, 6 , and 9 are in the Supporting Information.…”

C−C Coupling between an η3-Allyl Ligand and Carbon Nucleophiles in Molybdenum and Tungsten Complexes: Structural Characterization of the Key Intermediate This work was supported by the Ministerio de Ciencia y Tecnología (grants BQU2000-0220 and BQU2000-0219) and the FICYT (grants PR-01-GE-7 and PR-01-GE-4).

“…Similar reactions were conducted with Li (alkyl) or K (enolate) reagents to give the products indicated in Scheme 1. Available data for the trans ‐dicarbonyl complexes, reaction times, and references for the non‐commercial coupling products are given: 11: IR: $\tilde \nu$ =1841 s cm −1 , 2 h; 12 : commercial; 13 : $\tilde \nu$ =1840 s cm −1 , 31 P{ 1 H} NMR (CDCl 3 ): δ =−4.72, −18.79 (ABq, 2 J (P,P)=69.5 Hz), 30 min; 14 :16; 15 : $\tilde \nu$ =1845 s cm −1 , 40 min; 16: 17; 17 : $\tilde \nu$ =1840 s, 1689 s cm −1 , 31 P{ 1 H} NMR (CDCl 3 ): δ =67.27, 11.73 (ABq, 2 J (P,P)=26.8 Hz), 2 h; 18 :18; 19 : $\tilde \nu$ =1847 s, 1784 s cm −1 , 4 h; 20 :19; 21 : $\tilde \nu$ =1843 s, 1785 s cm −1 , 4 h; 22 : commercial. Experimental details for 2, 6 , and 9 are in the Supporting Information.…”