Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams

被引：109

作者：

Wu, Shangze ^{[1
]}

Zeng, Rong ^{[1
]}

Fu, Chunling ^{[1
]}

Yu, Yihua ^{[3
]}

Zhang, Xue ^{[2
]}

Ma, Shengming ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

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

[3] E China Normal Univ, Dept Phys, Shanghai Key Lab Magnet Resonance, Shanghai 200062, Peoples R China

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 04期

关键词：

N BOND FORMATION; PROTON-ABSTRACTION MECHANISM; EFFECTIVE CORE POTENTIALS; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; DIRECT ARYLATION; RHODIUM(III)-CATALYZED SYNTHESIS; RH(III)-CATALYZED SYNTHESIS; MOLECULAR CALCULATIONS; NITROGEN-HETEROCYCLES;

D O I：

10.1039/c5sc00092k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Rh(III) catalyzed formal [4 + 2 + 2] cyclization of N-pivaloyloxybenzamides 1 with 1,6-allene-enes 2 by C-H functionalization is reported. The reactions occur at room temperature and are compatible with air and moisture with a tolerance of many synthetically useful functional groups. The follow-up modifications of the products have been demonstrated. After careful mechanistic studies and DFT calculation, a reaction mechanism was proposed.

引用

页码：2275 / 2285

页数：11

共 136 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2]

[Anonymous], ORGANOMETALLIC CHEM

[3]

[Anonymous], ORGANOMETALLIC CHEM

[4] STRUCTURE ELUCIDATION OF 3 TETRAHYDROQUINOLYLIMIDAZOLE ALKALOIDS FROM MACRORUNGIA LONGISTROBUS CBCL (ACANTHACEAE) [J].

ARNDT, RR ;

EGGERS, SH ;

JORDAAN, A .

TETRAHEDRON, 1969, 25 (14) :2767-&

[5] Insertion reactions of allenes with transition metal complexes [J].

Bai, Tao ;

Ma, Shengming ;

Jia, Guochen .

COORDINATION CHEMISTRY REVIEWS, 2009, 253 (3-4) :423-448

[6] Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model [J].

Barone, V ;

Cossi, M .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (11) :1995-2001

[7] ANTIINSECTAN ALKALOIDS - SHEARININES-A-C AND A NEW PAXILLINE DERIVATIVE FROM THE ASCOSTROMATA OF EUPENICILLIUM-SHEARII [J].

BELOFSKY, GN ;

GLOER, JB ;

WICKLOW, DT ;

DOWD, PF .

TETRAHEDRON, 1995, 51 (14) :3959-3968

[8] Computational and synthetic studies on the cyclometallation reaction of dimethylbenzylamine with [IrCl2Cp*]2: role of the chelating base [J].

Boutadla, Youcef ;

Davies, David L. ;

Macgregor, Stuart A. ;

Poblador-Bahamonde, Amalia I. .

DALTON TRANSACTIONS, 2009, (30) :5887-5893

[9] C-C σ complexes of rhodium [J].

Brayshaw, Simon K. ;

Sceats, Emma L. ;

Green, Jennifer C. ;

Weller, Andrew S. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (17) :6921-6926

[10] Iron-Catalyzed Diastereoselective Synthesis of α-(Methoxycarbonyl)allylsilanes [J].

Chai, Guobi ;

Zeng, Rong ;

Fu, Chunling ;

Ma, Shengming .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (01) :148-154

← 1 2 3 4 5 6 7 8 9 10 →