Transition-Metal-Catalyzed Silylation and Borylation of C-H Bonds for the Synthesis and Functionalization of Complex Molecules

被引:83
作者
Yu, Isaac F. [1 ]
Wilson, Jake W. [1 ]
Hartwig, John F. [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
LATE-STAGE FUNCTIONALIZATION; POLYCYCLIC AROMATIC-HYDROCARBONS; HEXA-PERI-HEXABENZOCORONENES; PORPHYRIN PINCER COMPLEXES; VERSATILE BUILDING-BLOCKS; CROSS-COUPLING REACTIONS; C(SP(3))-H BORYLATION; WARPED NANOGRAPHENE; BODIPY DYES; REGIOSPECIFIC FUNCTIONALIZATION;
D O I
10.1021/acs.chemrev.3c00207
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The functionalization of C-H bonds in organic molecules containing functional groups has been one of the holy grails of catalysis. One synthetically important approach to the diverse functionalization of C-H bonds is the catalytic silylation or borylation of C-H bonds, which enables a broad array of downstream transformations to afford diverse structures. Advances in both undirected and directed methods for the transition-metal-catalyzed silylation and borylation of C-H bonds have led to their rapid adoption in early-, mid-, and late-stage of the synthesis of complex molecules. In this Review, we review the application of the transition-metal-catalyzed silylation and borylation of C-H bonds to the synthesis of bioactive molecules, organic materials, and ligands. Overall, we aim to provide a picture of the state of art of the silylation and borylation of C-H bonds as applied to the synthesis and modification of diverse architectures that will spur further application and development of these reactions.
引用
收藏
页码:11619 / 11663
页数:45
相关论文
共 290 条
[41]   Subphthalocyanines, Subporphyrazines, and Subporphyrins: Singular Nonplanar Aromatic Systems [J].
Claessens, Christian G. ;
Gonzalez-Rodriguez, David ;
Salome Rodriguez-Morgade, M. ;
Medina, Anais ;
Torres, Tomas .
CHEMICAL REVIEWS, 2014, 114 (04) :2192-2277
[42]   Validation of the M-C/H-C bond enthalpy relationship through application of density functional theory [J].
Clot, Eric ;
Megret, Claire ;
Eisenstein, Odile ;
Perutz, Robin N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) :8350-8357
[43]   meta-selective aromatic borylation as key step in the synthesis of poipuol [J].
Cordes, Jens ;
Wessel, Claas ;
Harms, Klaus ;
Koert, Ulrich .
SYNTHESIS-STUTTGART, 2008, (14) :2217-2220
[44]   Selective Ir-catalysed borylation of polycyclic aromatic hydrocarbons: structures of naphthalene-2,6-bis(boronate), pyrene-2,7-bis(boronate) and perylene-2,5,8,11-tetra(boronate) esters [J].
Coventry, DN ;
Batsanov, AS ;
Goeta, AE ;
Howard, JAK ;
Marder, TB ;
Perutz, RN .
CHEMICAL COMMUNICATIONS, 2005, (16) :2172-2174
[45]   Synthesis of 2-and 2,7-Functionalized Pyrene Derivatives: An Application of Selective C-H Borylation [J].
Crawford, Andrew G. ;
Liu, Zhiqiang ;
Mkhalid, Ibraheem A. I. ;
Thibault, Marie-Helene ;
Schwarz, Nicolle ;
Alcaraz, Gilles ;
Steffen, Andreas ;
Collings, Jonathan C. ;
Batsanov, Andrei S. ;
Howard, Judith A. K. ;
Marder, Todd B. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) :5022-5035
[46]   Phosphine-Directed C-H Borylation Reactions: Facile and Selective Access to Ambiphilic Phosphine Boronate Esters [J].
Crawford, Kristina M. ;
Ramseyer, Timothy R. ;
Daley, Christopher J. A. ;
Clark, Timothy B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (29) :7589-7593
[47]   Ir-catalyzed C-H activation in the synthesis of borylated ferrocenes and half sandwich compounds [J].
Datta, A ;
Köllhofer, A ;
Plenio, H .
CHEMICAL COMMUNICATIONS, 2004, (13) :1508-1509
[48]   Ru-catalysed C-H silylation of unprotected gramines, tryptamines and their congeners [J].
Devaraj, K. ;
Sollert, C. ;
Juds, C. ;
Gates, P. J. ;
Pilarski, L. T. .
CHEMICAL COMMUNICATIONS, 2016, 52 (34) :5868-5871
[49]   TRANSFER DEHYDROGENATIVE COUPLING OF TRIETHYLSILANE CATALYZED BY RUTHENIUM AND RHODIUM COMPLEXES - A NEW SI-C BOND-FORMING PROCESS [J].
DJUROVICH, PI ;
DOLICH, AR ;
BERRY, DH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (16) :1897-1898
[50]   Iron-Catalyzed C-H Borylation of Arenes [J].
Dombray, Thomas ;
Werncke, C. Gunnar ;
Jiang, Shi ;
Grellier, Mary ;
Vendier, Laure ;
Bontemps, Sebastien ;
Sortais, Jean-Baptiste ;
Sabo-Etienne, Sylviane ;
Darcel, Christophe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (12) :4062-4065