Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation was written by Ni, Hui-Qi;Kevlishvili, Ilia;Bedekar, Pranali G.;Barber, Joyann S.;Yang, Shouliang;Tran-Dube, Michelle;Romine, Andrew M.;Lu, Hou-Xiang;McAlpine, Indrawan J.;Liu, Peng;Engle, Keary M.. And the article was included in Nature Communications in 2020.Product Details of 207115-22-8 This article mentions the following:
A method that enables direct access to these core structures, e.g., I from non-conjugated alkenyl amides RNHC(O)CH(R2)CH=CHR1 [R = quinolin-8-yl, pyridin-2-yl; R1 = H, Me, Et; R2 = H, CH3, CH2C6H5, 3-CH3OC6H4(CH2)2, (CH2)2OCH2C6H5, (CH2)2CH=CH2] and N-3-buten-1-yl-2-pyridinecarboxamide and ortho-iodoanilines, e.g., 4-iodopyridin-3-amine/phenols II (R3 = Me, Br, t-Bu, etc.; R4 = H, Br; R5 = H, I; X = O) has been described. Under palladium(II) catalysis this [3 + 2] heteroannulation proceeds in an anti-selective fashion and tolerates a wide variety of functional groups. N-Acetyl, -tosyl, and -alkyl substituted ortho-iodoanilines, as well as free -NH2 variants, are all effective. Preliminary results with carbon-based coupling partners like Et 2-cyano-2-(2-iodophenyl)acetate, di-Me 2-(2-iodophenyl)malonate and Et 2-(benzenesulfonyl)-2-(2-iodophenyl)acetate also demonstrate the viability of forming indane core structures III (R6 = C(O)2Me, C(O)2Et; R7 = C(O)2Me, CN, S(O)2Ph) using this approach. Exptl. and computational studies on reactions with phenols support a mechanism involving turnover-limiting, endergonic directed oxypalladation, followed by intramol. oxidative addition and reductive elimination. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Product Details of 207115-22-8).
4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Product Details of 207115-22-8
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com