Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions

被引：40
|
作者：
Munoz, Socrates B. [1 ,2 ]
Aloia, Alexandra N. [1 ,2 ]
Moore, Alexander K. [1 ,2 ]
Papp, Attila [1 ,2 ]
Mathew, Thomas [1 ,2 ]
Fustero, Santos [3 ,4 ]
Olah, George A. [1 ,2 ]
Prakash, G. K. Surya [1 ,2 ]
机构：
[1] Univ So Calif, Loker Hydrocarbon Res Inst, Los Angeles, CA 90089 USA
[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
[3] Univ Valencia, Dept Quim Organ, E-46012 Valencia, Spain
[4] Ctr Invest Principe Felipe, Lab Mol Organ, E-46012 Valencia, Spain
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 01期
关键词：
ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HIGHLY REGIO; SUBSTITUTED; 3-METHYLENEISOINDOLIN-1-ONES; INTRAMOLECULAR CYCLIZATION; ASYMMETRIC-SYNTHESIS; PALLADIUM; ARYL; ALKYNYLSILANES; ALKYNES;
D O I：
10.1039/c5ob02187a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl) alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently "unmasked" upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene (TMSA) as a convenient acetylene surrogate was also shown to be feasible under Pd/Cu catalysis.
引用
收藏
页码：85 / 92
页数：8
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