Synthesis of Substituted Styrenes and 3-Vinylphenols Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis

Abstract

The synthesis of substituted styrenes 3 and 3-vinylphenols 9 was achieved by ring-closing enyne metathesis (RCEM)/dehydration of 7 and RCEM/tautomerization of 8, respectively. Those methods provide selective access to unique aromatic compounds and solve the problem of regioisomer formation.

Lanthanum-Catalyzed Regioselective Anti-Markovnikov Hydrophosphinylation of Styrenes

“…Styrene substrates were purchased from Oakwood, Alfa, Aldrich, Acros, or AK Scientific. Styrene substrates for products 3d , e , j , o – q were synthesized according to literature reports . All styrene substrates were dried over calcium hydride, filtered, freeze–pump–thawed three times, and stored in a nitrogen-filled glovebox.…”

“…Legend for alternative reaction conditions: (#) alkene 1a (0.25 mmol), diarylphosphine oxide 2 (0.4 mmol), La(DMBA) 3 (5 mol %, 0.0125 mmol, 6.775 mg), pyridine (0.75 mL), 16 literature reports. 32 All styrene substrates were dried over calcium hydride, filtered, freeze−pump−thawed three times, and stored in a nitrogen-filled glovebox. Pyridine was purchased from Acros, dried over sodium metal, distilled under nitrogen, freeze−pump−thawed three times, and stored in a nitrogen-filled glovebox.…”

An efficient synthesis of 6‐benzyl‐2‐arylthieno[2,3‐d]pyrimidin‐4(3H)‐ones catalyzed by HCl involving a Friedel‐Crafts alkylation reaction

“…The 2‐(2‐phenylethynyl)benzaldehydes ( 2 ) were prepared by a known reaction of 2‐bormobenzaldehydes and terminal acetylenes. [ 14a ]…”

Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes

“…Spectroscopic data are consistent with those previously reported. 17 Ag catalyst 36-endo-dig cyclization A. D. Sonawane et al…”