Quality Control of Picolinoyl chloride hydrochloride. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Picolinoyl chloride hydrochloride, is researched, Molecular C6H5Cl2NO, CAS is 39901-94-5, about Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation. Author is 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..
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.
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