4-Iodobenzoyl chloride

A complementary approach to six-membered rings can be achieved with methyl 2-iodobenzoate or 2-iodobenzoyl chloride, as shown in Scheme 16 (Grigg et al. 2002). 

A palladium-catalyzed three-component reaction with 2-iodobenzoyl chloride or methyl 2-iodobenzoate, allene and primary aliphatic or aromatic amines to prepare fV-substituted 4-methylene-3,4-dihydro-1 (27/)-isoquinolin-1 -ones was disclosed <02TL2601>. A synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines via a Cp2TiMe2-catalyzed, intramolecular hydroamination/cyclization of aminoalkynes was also reported <02TL3715>. Additionally, a palladium-catalyzed one-atom ring expansion of methoxyl allenyl compounds 79 to prepare compounds 80 that can serve as precursors to isoquinolones was reported <02OL455,02SL480>. 

The latter process must play a key role in the recently reported Pd-catalyzed alternative copolymerization of ethene and CO in water. It is also involved as a mechanistic step in a new synthesis of isoindolin-l-ones 40 by Pd-catalyzed intermolecular coupling and heteroannelation between 2-iodobenzoyl chloride (37) and imines 38 (Scheme 11). In this case, however, a /3-hydride elimination in the intermediate 39 would not be possible at all. 

A novel, three-component, palladium-catalyzed, cascade cyclization-anion-capture process which involves in situ generation of a zipper molecule has been reported. Thus, 2-iodobenzoyl chloride, an acetophenone imine, and carbon monoxide react in the presence of Pd(PPh3)2Cl2 to give isoindolin-l-one in moderate yield (eq 86). 

Cho, C.S., Shim, S.C., Choi, H.-J., Kim, T.-J., Shim, S.C. and Kim, M.C. (2000) Synthesis of isoindolin-l-ones via palladium-catalyzed intermolecular coupling and heteroannulation between 2-iodobenzoyl chloride and imines. Tetrahedron Letters, 41, 3891-3893. 

Two substrates for Suzuki couplings were immobilized exposing the support (14) to o- or p-iodobenzoyl chloride. After purification on a Sephadex LH-20 SFC... 

A synthesis of racemic fmoc-protected 4-phosphonomethylphenylalanine starts with the Arbuzov preparation of (257) (R = Me or Bu ) standard modifications to the aryl methyl group lead to the desired (258). Two procedures have been adopted for the preparation of the N-ivaoc or iV-boc derivatives of the difluoro derivative (259). In the first, triethyl phosphite and 4-(bromomethyl)benzoyl bromide and treatment of the resultant aroyl phosphonate with the DAST reagent yields (262) this reacts with the carbanion from (263) to give (264) hydrogenation of which (with PdCla) affords (260), then converted into its N-fmoc derivative and de-esterified with MeaSil. In the second procedure, triethyl phosphite and 4-iodobenzoyl chloride, followed by DAST reagent, yielded diethyl [difluoro(4-iodophenyl)methyl]phosphonate which was caused to react... 

Gholesteryl-4-iodobenzoate-P has been prepared from cholesterol in 90-96% yield according to the procedure of Stokes et al. (1954). The first product of the reaction, 4-iodobenzoic-P acid, is prepared from I2, Nal , and 4-chloromercuribenzoic acid. The 4-iodobenzoic-P acid reacts with an acyl chloride to give 4-iodobenzoyl-P S which then reacts widr cholesterol. 

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