Harada, Yasuyuki published the artcileRh(I)-Catalyzed Carbonylative Cyclization Reactions of Alkynes with 2-Bromophenylboronic Acids Leading to Indenones, Application of 2-Bromo-5-methoxybenzene boronic acid, the publication is Journal of the American Chemical Society (2007), 129(17), 5766-5771, database is CAplus and MEDLINE.
The Rh-catalyzed reaction of alkynes with 2-bromophenylboronic acids involves carbonylative cyclization to give indenones. The key steps in the reaction involve the addition of an arylrhodium(I) species to an alkyne and the oxidative addition of C-Br bonds on the adjacent Ph ring to give vinylrhodium(I) species II. The regioselectivity depends on both the electronic and the steric nature of the substituents on the alkynes. A bulky group and an electron-withdrawing group favor the α-position of indenones. In the case of silyl- or ester-substituted alkynes, the regioselectivity is extremely high. The selectivity increases in the order SiMe3 > COOR ≫ aryl ≫ alkyl. The reaction of norbornene with 2-bromophenylboronic acids under 1 atm of CO gives the corresponding indanone derivative The reaction of alkynes with 2-bromophenylboronic acids under nitrogen gives naphthalene derivatives, in which two mols. of alkynes are incorporated. A vinylrhodium complex similar to II can also be generated by a different route by employing 2-bromophenyl(trimethylsilyl)acetylene and arylboronic acids in the presence of Rh(I) complex as the catalyst, resulting in the formation of indenones. The reaction of 1-(2-bromophenyl)-hept-2-yn-1-one with PhB(OH)2 in the presence of Rh(I) complex also resulted in carbonylative cyclization to give an indan-1,3-dione derivative
Journal of the American Chemical Society published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Application of 2-Bromo-5-methoxybenzene boronic acid.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary