Reaction of Propargyl Bromide with Aldehydes in the Presence of Metallic Tin. Synthesis of Homopropargylalcohols and Homoallenylalcohols

CuI‐Catalyzed Synthesis of Functionalized Terminal Allenes from 1‐Alkynes

“…1‐(3‐Nitrophenyl)‐2,3‐butadien‐1‐ol (2f): The reaction of CuI (142.5 mg, 0.75 mmol), paraformaldehyde (480.5 mg, 16.00 mmol), 1f (1.7732 g, 10.00 mmol), and i Pr 2 NH (2.0 mL, d = 0.716 g mL –1 , 1.432 g, 14.15 mmol) in dioxane (15 mL) afforded 2f 11b (1.5460 g, 81 %) after purification (eluent for chromatography: petroleum ether/ethyl acetate, 5:1) as a liquid. 1 H NMR (300 MHz, CDCl 3 ): δ = 8.24 (s, 1 H, ArH), 8.10 (d, J = 7.8 Hz, 1 H, ArH), 7.72 (d, J = 7.8 Hz, 1 H, ArH), 7.50 (t, J = 7.6 Hz, 1 H, ArH), 5.46–5.32 (m, 2 H, C=CH and OCH), 5.00–4.86 (m, 2 H, C=CH 2 ), 2.84–2.55 (m, 1 H, OH) ppm.…”

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

“…The reaction of propargyl bromide with aldehydes mediated by tin in water generated a mixture of propargylation and allenylation products. The selectivity in product formation is rather low . Allenylations and propargylations of carbonyl compounds in aqueous media could also be carried out with the preformed organic tin reagents, instead of using metals. − The combination of SnCl 2 and KI was found to be more effective for the reaction (eq 100) …”

“…The selectivity in product formation is rather low. 354 Allenylations and propargylations of carbonyl compounds in aqueous media could also be carried out with the preformed organic tin reagents, instead of using metals. [355][356][357][358] The combination of SnCl 2 and KI was found to be more effective for the reaction (eq 100).…”

The Versatility of α-Chloropropargyl Phenyl Sulfide Affords High Stereo- and Regioselectivities in Indium-Promoted Coupling Reactions under Mild Conditions

“…Stereo- and Regioselectivity Studies with Propargyl Sulfides. Stereoselective formation of epoxy alkynes ( 14 ) has emerged as an area of increasing interest in recent years due to their unique skeletal design and use in formation of more complicated structural systems. , Procedures applied in formation of epoxy alkynes such as use of m -CPBA and oxone and ring closure of halohydrin precursors have been successful, but only a limited number of examples are found in the literature . An indium-based methodology using propargyl sulfides such as shown in entries 20−23 (Table ) would offer a nice addition in this area of chemistry. − …”