Recent Advances in Direct C-H Bond Functionalization of Phenylalanine Derivatives

被引:5
作者
Li, Xiaofang [1 ]
Xiong, Weikang [1 ]
Ding, Qiuping [1 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Key Lab Small Funct Organ Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
phenylalanine; C-H functionalization; alkylation; alkenylation; arylation; REGIOSPECIFIC SYNTHESIS; NITRATION; PICOLINAMIDE; NITROARENES; ACTIVATION; AMINATION; ARYLATION; DELTA; SP(2);
D O I
10.6023/cjoc201901029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenylalanine derivatives are widely found in a broad range of pharmaceutical molecules and exhibit significant biological activity. Direct C-H bond functionalization of phenylalanine derivatives to offer an efficient approach to construct C-I, C(sp(2))-C(sp(2)), C(sp(2))-C(sp), C(sp(2))-C(sp(3)), C-N, C-B and C-O bonds is described. The transformation involves ortho-C-H bond iodination and the following intramolecular amination, ortho-alkylation, ortho-arylation, ortho-alkenylation, ortho-alkynylation, ortho-acylation, ortho-acetoxylation, ortho-amination, ortho-boronation, meta-arylation and meta-alkylation.
引用
收藏
页码:1867 / 1874
页数:8
相关论文
共 39 条
[1]   Direct ortho iodination of β- and γ-aryl alkylamine derivatives [J].
Barluenga, Jose ;
Alvarez-Gutierrez, Julia M. ;
Ballesteros, Alfredo ;
Gonzalez, Jose M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (08) :1281-1283
[2]   Rhodium-Catalyzed C-H Bond Arylation of Arenes [J].
Bouffard, Jean ;
Itami, Kenichiro .
C-H ACTIVATION, 2010, 292 :231-280
[3]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[4]   Ligand-Enabled meta-Selective C-H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines [J].
Ding, Qiuping ;
Ye, Shengqing ;
Cheng, Guolin ;
Wang, Peng ;
Farmer, Marcus E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) :417-425
[5]   Pd-Catalyzed Directed ortho-C-H Alkenylation of Phenylalanine Derivatives [J].
Garcia-Rubia, Alfonso ;
Laga, Eduardo ;
Cativiela, Carlos ;
Urriolabeitia, Esteban P. ;
Gomez-Arrayas, Ramon ;
Carretero, Juan C. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (06) :3321-3331
[6]   Eluxadoline: First Global Approval [J].
Garnock-Jones, Karly P. .
DRUGS, 2015, 75 (11) :1305-1310
[7]   Palladium-catalyzed oxalyl amide assisted direct ortho-alkynylation of arylalkylamine derivatives at δ and ε positions [J].
Guan, Mingyu ;
Chen, Changpeng ;
Zhang, Jingyu ;
Zeng, Runsheng ;
Zhao, Yingsheng .
CHEMICAL COMMUNICATIONS, 2015, 51 (60) :12103-12106
[8]   Could a combined administration of dexamethasone and 3,5-dimethyl-3′-isopropyl-L-thyronine (DIMIT) be a more effective alternative to dexamethasone alone in the prevention of RDS? [J].
Halis, G ;
Ragosch, V ;
Kuhlmann, K ;
Ebert, AD ;
Hundertmark, S .
EUROPEAN JOURNAL OF OBSTETRICS GYNECOLOGY AND REPRODUCTIVE BIOLOGY, 2001, 99 (02) :188-194
[9]   Borylation and Silylation of C-H Bonds: A Platform for Diverse C-H Bond Functionalizations [J].
Hartwig, John F. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :864-873
[10]   Improved Protocol for Indoline Synthesis via Palladium-Catalyzed Intramolecular C(sp2)-H Amination [J].
He, Gang ;
Lu, Chengxi ;
Zhao, Yingsheng ;
Nack, William A. ;
Chen, Gong .
ORGANIC LETTERS, 2012, 14 (12) :2944-2947