Ni(II)-Catalyzed C(sp2)-H Alkynylation/Annulation with Terminal Alkynes under an Oxygen Atmosphere: A One-Pot Approach to 3-Methyleneisoindolin-1-one

被引：71

作者：

Zheng, Xin-Xiang ^{[1
]}

Du, Cong ^{[1
]}

Zhao, Xue-Mei ^{[1
]}

Zhu, Xinju ^{[1
]}

Suo, Jian-Feng ^{[1
]}

Hao, Xin-Qi ^{[1
]}

Niu, Jun-Long ^{[1
]}

Song, Mao-Ping ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 10期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; 1ST TOTAL-SYNTHESIS; ALIPHATIC AMIDES; OXIDATIVE ALKENYLATION/ANNULATION; STEREOSELECTIVE-SYNTHESIS; CATALYZED CYCLIZATION; ANNULATION; ACTIVATION; C(SP(3))-H; ALKENES;

D O I：

10.1021/acs.joc.6b00129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel(II)-catalyzed alkynylation/annulation cascade via double C-H cleavage has been successfully achieved. This methodology adopted a removable N,O-bidentate directing group with a broad range of amide substrates and terminal alkynes being well tolerated. The catalytic system allowed for atom-economical and environmentally benign one-pot construction of the corresponding 3-methyleneisoindolin-1-one derivatives using O-2 as the external oxidant.

引用

页码：4002 / 4011

页数：10

共 62 条

[21] Reductive Coupling of Phthalimides with Ketones and Aldehydes by Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones [J].

Kise, Naoki ;

Kawano, Yusuke ;

Sakurai, Toshihiko .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24) :12453-12459

[22] A Convenient Synthesis of 2,3-Dihydro-3-methylidene-1H-isoindol-1-ones by Reaction of 2-Formylbenzonitriles with Dimethyloxosulfonium Methylide [J].

Kobayashi, Kazuhiro ;

Matsumoto, Kota ;

Nakamura, Daizo ;

Fukamachi, Shuhei ;

Konishi, Hisatoshi .

HELVETICA CHIMICA ACTA, 2010, 93 (06) :1048-1051

[23]

Laboratori Baldacci S. p. A, [No title captured], Patent No. [JP 59046268, 59046268]

[24] A concise first total synthesis of narceine imide [J].

Lamblin, Marc ;

Couture, Axel ;

Deniau, Eric ;

Grandclaudon, Pierre .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (09) :1466-1471

[25] Nickel-catalyzed direct alkynylation of C(sp2)-H bonds of amides: an "inverse Sonogashira strategy" to ortho-alkynylbenzoic acids [J].

Landge, Vinod G. ;

Shewale, Chinmay H. ;

Jaiswal, Garima ;

Sahoo, Manoj K. ;

Midya, Siba P. ;

Balaraman, Ekambaram .

CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (06) :1946-1951

[26] Assembly of Substituted 3-Methyleneisoindolin-1-ones via a CuI/L-Proline-Catalyzed Domino Reaction Process of 2-Bromobenzamides and Terminal Alkynes [J].

Li, Li ;

Wang, Miao ;

Zhang, Xiaojing ;

Jiang, Yongwen ;

Ma, Dawei .

ORGANIC LETTERS, 2009, 11 (06) :1309-1312

[27] Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C-H Bonds with Alkynes: A Concise Route to Polysubstituted γ-Butyrolactones [J].

Li, Mingliang ;

Yang, Yudong ;

Zhou, Danni ;

Wan, Danyang ;

You, Jingsong .

ORGANIC LETTERS, 2015, 17 (10) :2546-2549

[28] Oxidative Alkenylation/Annulation of Benzimidates via Ruthenium(II)-Catalyzed C-H Activation to Generate 3-Methyleneisoindolin-1-ones [J].

Li, Xing Guang ;

Sun, Min ;

Liu, Kai ;

Liu, Pei Nian .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :395-399

[29] Direct ortho-Thiolation of Arenes and Alkenes by Nickel Catalysis [J].

Lin, Cong ;

Li, Danyang ;

Wang, Binjie ;

Yao, Jinzhong ;

Zhang, Yuhong .

ORGANIC LETTERS, 2015, 17 (05) :1328-1331

[30] Ni(II)-catalyzed dehydrative alkynylation of unactivated (hetero) aryl C-H bonds using oxygen: a user-friendly approach [J].

Liu, Yan-Hua ;

Liu, Yue-Jin ;

Yan, Sheng-Yi ;

Shi, Bing-Feng .

CHEMICAL COMMUNICATIONS, 2015, 51 (58) :11650-11653

← 1 2 3 4 5 6 7 →