A Convenient Synthesis of 2-Arylbenzo[b]furans from Aryl Halides and 2-Halophenols by Catalytic One-Pot Cascade Method

Abstract

The development of a multicatalytic one-pot synthesis of 2-arylbenzofurans starting from aryl halides and 2-halophenols is described. The protocol involves two Sonogashira coupling reactions, followed by 2-ethynylphenol cyclization leading to 2-arylbenzofuran derivatives. The process occurs smoothly under mild conditions, giving products in good yields, and can be applied to many 2-arylbenzofurans substituted both at 2-aryl position and in the benzodifuran moiety. Substituents such as halogens, hydroxyl, cyano, nitro, and amino groups are tolerated, enabling further functionalization of the system.

Access to Multifunctionalized Benzofurans by Aryl Nickelation of Alkynes: Efficient Synthesis of the Anti‐Arrhythmic Drug Amiodarone

“…[15] Thek ey substituted benzofuran ring system, 3hf,ofamiodarone was constructed in asingle step in 88 %y ield by using 1h and 4-hydroxy phenylboronic acid (2f). [16] Subsequent phenol ring iodination [17] and O-alkylation [18] generated 15. [16] Subsequent phenol ring iodination [17] and O-alkylation [18] generated 15.…”

Synthesis of o‐Allyloxy(ethynyl)benzene Derivatives by Cu‐Catalyzed Suzuki–Miyaura‐Type Reaction and Their Transformations into Heterocyclic Compounds

“…: [28] 5, 139.9, 132.9, 131.6, 129.4, 127.9, 125.5, 123.3, 115.6, 114.0, 93.3, 87.0, 55.3, 20.7 5, 137.0, 135.7, 130.8, 129.5, 129.1, 128.53, 128.46, 127.0, 126.1, 38.9, 21. (5): [38] 154.7, 138.6, 129.5, 129.3, 127.7, 124.9, 124.0, 122.8, 120.7, 111.1, 100.5, 21.4 35-7.19 (m, 9 H), 7.07 (td, J = 7.6, 0.9 Hz, 1 H), 6.53-6.42 (m, 1 H), 5.30 (dt, J = 10.1, 1.5 Hz, 1 H), 5.20 (d, J = 6.5 Hz, 1 H), 5.13 (dt, J = 17.1, 1.5 Hz, 1 H), 2.41 (s, 3 H) ppm. 13 C NMR (75 MHz, CDCl 3 ): δ = 154.…”

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

“…Substituents at the benzene moiety often originate from the synthetic precursor used to construct the benzofuran scaffold. Synthetic methods for assembling the benzofuran scaffold have typically involved acid-catalyzed cyclizations [11][12][13][14][15][16][17], carbonylative cyclizations via Sonogashira reactions [18][19][20][21][22][23][24], Heck-type cyclizations [25][26][27][28][29], photocyclizations [30][31][32][33][34], radical cyclizations [35][36][37][38][39], and other types of transition-metal catalyzed transformations [40][41][42][43][44][45]. When it comes to the functionalization of the furan part, there exists a considerable number of methods for directly functionalizing either the C2 or C3 position [46][47][48][49][50][51][52][53][54][55][56].…”