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

页码：85 / 92

页数：8