Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.Recommanded Product: 2635-13-4
Moriguchi, Kento; Sasaki, Ryosuke; Morita, Jun-ichi; Kamakura, Yoshinobu; Tanaka, Daisuke; Tanabe, Yoo published their research in ACS Omega in 2021. The article was titled 《Ipso-Type Regiocontrolled Benzannulation for the Synthesis of Uniquely Substituted α-Arylnaphthalenes: Application to the First Total Synthesis of Chaihunaphthone》.Recommanded Product: 2635-13-4 The article contains the following contents:
A distinctive method for synthesizing a variety of multisubstituted α-arylnaphthalenes utilizing novel regiocontrolled ipso-type [4+2]-benzannulation is presented. Ortho- and para-substituted 1-Ar1-1-Ar2-2,2-dichlorocyclopropylmethanols (AACM), I [R1 = H, Ar1 = Ph, 2-MeC6H4, 3-MeOC6H4, 2-ClC6H4, Ar2 = 2-MeC6H4, 2-ClC6H4, 2-MeOC6H4, 4-MeC6H4, 4-ClC6H4, 4-MeOC6H4; R1 = Me, Ar1 = Ph, 2-MeC6H4, 2-MeOC6H4, 3-MeOC6H4, Ar2 = 4-MeC6H4, 4-ClC6H4], were transformed to the corresponding ipso-type α-arylnaphthalenes II (Ar1 = Ph, 2-MeC6H4, 2-ClC6H4, 2-MeOC6H4, R2 = Me, Cl, OMe), and III (R1 = H, Me, R2 = Me, Cl, OMe, Ar1 = Ph, 2- MeC6H4, 2-ClC6H4, 2-MeOC6H4, 3-MeOC6H4, 4-MeC6H4). The reaction of ortho-AACM using TiCl4 or SnCl4 (1.0 equiv) proceeded smoothly to afford ipso-type α-arylnaphthalenes (seven examples; 49-69% yield) exclusively, without producing conventional benzannulation isomers. Para-AACM also underwent the reaction successfully to afford the desired ipso-type α-arylnaphthalenes (14 examples; 39-98% yield) without producing conventional benzannulation isomers. In contrast, meta-AACM underwent the previously reported conventional benzannulation. The present method exhibited sufficient substrate generality for application to ortho- and para-substituted AACM substrates bearing Me-, Cl-, and MeO- groups. The six key structures were unambiguously confirmed by X-ray structure analyses. A plausible reaction mechanism for the present ipso-type reaction is proposed and supported by three careful cross-over and comparable experiments To demonstrate the utility of the present reaction, the authors achieved the first total synthesis of chaihunaphthone, IV, a uniquely (highly congested) substituted and less accessible natural lignan lactone with three contiguous trimethoxy substituents (total of eight steps, overall 6.4% yield). In the experimental materials used by the author, we found 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4Recommanded Product: 2635-13-4)
Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.Recommanded Product: 2635-13-4
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary