Rhodium(III)-Catalyzed C-H Activation and Annulation with 1-Alkynylphosphine Sulfides: A Mild and Regioselective Access for the Synthesis of Bulky Phosphine Ligands

被引：37

作者：

Li, Bin ^{[1
]}

Yang, Jie ^{[1
]}

Xu, Hong ^{[1
]}

Song, Haibin ^{[1
]}

Wang, Baiquan ^{[1
,2
,3
]}

机构：

[1] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

[2] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 24期

基金：

中国国家自然科学基金;

关键词：

OXIDIZING DIRECTING GROUP; (ELECTRON-DEFICIENT ETA(5)-CYCLOPENTADIENYL)RHODIUM(III) CATALYST; N BOND FORMATION; INTERNAL ALKYNES; OXIDATIVE ANNULATION; 2+2+2 CYCLOADDITION; AMBIENT CONDITIONS; ENANTIOSELECTIVE SYNTHESIS; CROSS-CYCLOTRIMERIZATION; ISOQUINOLONE SYNTHESIS;

D O I：

10.1021/acs.joc.5b02265

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We reported herein rhodium(III)-catalyzed C-H activation and annulation reactions for the synthesis of bulky phosphine ligands by using 1-alkynylphosphine sulfides as key starting materials. In the presence of [Cp*RhCl2](2) (5 mol %) and Cs0Ac (2.0 equiv), various N-(pivaloyloxy)benzamides (3.0 equiv) could react smoothly with 1-alkynylphosphine sulfides at 40 degrees C in MeOH/CF3CH2OH cosolvent without external oxidant. Using [(CpRhCl2)-Rh-Ph](2) as catalyst, the reaction can be performed under less loading of benzamides (2.0 equiv) and milder reaction conditions (25 degrees C) with higher regioselectivity. In a sequential cydization/desulfidation process, this new method provides a variety of bulky heteroarylphosphines with an isoquinolin-1(2H)-one motif.

引用

页码：12397 / 12409

页数：13

共 90 条

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