New Approaches to the Synthesis of Metal Carbenes

被引：303

作者：

Jia, Minqiang ^{[1
]}

Ma, Shengming ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 32期

关键词：

diazo compounds; homogeneous catalysis; metal carbenes; surrogates; synthetic methods; GOLD-CATALYZED CYCLOISOMERIZATION; C-H INSERTION; IN-SITU GENERATION; ENE-YNE-KETONES; RHODIUM(II)-CATALYZED STEREOCONTROLLED SYNTHESIS; TERMINAL ALKYNES SYNTHESIS; HIGHLY EFFICIENT SYNTHESIS; RETRO-BUCHNER REACTION; DOYLE-KIRMSE REACTION; MEDIUM-SIZED RINGS;

D O I：

10.1002/anie.201508119

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Metal carbenes usually possess versatile reactivities that are controlled by the presence of both the metals and the ligands. Diazo compounds are commonly used for the generation of such species through elimination of nitrogen. However, they are often unstable, explosive, and toxic, which limits their applications in large-scale syntheses. Thus, identifying sustainable and safe surrogates for the generation of metal carbenes has attracted great attention. In this Review, we summarize some of the most important breakthroughs in the generation, catalytic reactions, and selectivity control of metal carbenes from non-diazo starting compounds.

引用

页码：9134 / 9166

页数：33

共 522 条

[1] Regioselective syntheses of fully-substituted 1,2,3-triazoles: the CuAAC/C-H bond functionalization nexus [J].

Ackermann, Lutz ;

Potukuchi, Harish Kumar .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4503-4513

[2] Diastereoselective synthesis of cyclopropane amino acids using diazo compounds generated in situ [J].

Adams, LA ;

Aggarwal, VK ;

Bonnert, RV ;

Bressel, B ;

Cox, RJ ;

Shepherd, J ;

de Vicente, J ;

Walter, M ;

Whittingham, WG ;

Winn, CL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9433-9440

[3]

Aggarwal K., 2003, ANGEW CHEM, V115, P3396

[4]

Aggarwal V.K., 2001, ANGEW CHEM, V113, P1482

[5]

Aggarwal V.K., 2001, Angew. Chem, V113, P1479

[6] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[7] Effect of sulfide structure on enantioselectivity in catalytic asymmetric epoxidation of aldehydes: Mechanistic insights and implications [J].

Aggarwal, VK ;

Charmant, J ;

Dudin, L ;

Porcelloni, M ;

Richardson, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5467-5471

[8] Asymmetric sulfur ylide mediated aziridination: Application in the synthesis of the side chain of taxol [J].

Aggarwal, VK ;

Vasse, JL .

ORGANIC LETTERS, 2003, 5 (21) :3987-3990

[9] A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities [J].

Aggarwal, VK ;

Alonso, E ;

Bae, I ;

Hynd, G ;

Lydon, KM ;

Palmer, MJ ;

Patel, M ;

Porcelloni, M ;

Richardson, J ;

Stenson, RA ;

Studley, JR ;

Vasse, JL ;

Winn, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10926-10940

[10] Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; Application to the synthesis of CDP-840 [J].

Aggarwal, VK ;

Bae, I ;

Lee, HY ;

Richardson, J ;

Williams, DT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (28) :3274-3278

← 1 2 3 4 5 6 7 8 9 10 →