Catalyst-enabled Site-selectivity in the Iridium-catalyzed C-H Borylation of Arenes

被引：51

作者：

Kuroda, Yusuke ^{[1
]}

Nakao, Yoshiaki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Mat Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

CHEMISTRY LETTERS | 2019年 / 48卷 / 09期

关键词：

C-H borylation; Iridium; Site-selectve; NONCOVALENT INTERACTIONS; DIRECTING GROUP; LIGAND; COMPLEXES; BONDS; REGIOSELECTIVITY; REAGENTS; NITROGEN; FUNCTIONALIZATION; ORGANOBORANES;

D O I：

10.1246/cl.190372

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct and selective replacement of C-H bonds in aromatic compounds with C-B bonds represents an ideal approach to arylboron compounds. Despite the tremendous advances during the past fifteen years, controlling the site-selectivity has remained a central challenge in this field. This Highlight Review summarizes the recent progress on the site-selective C-H borylation of arenes with a particular focus on the factors guiding the site-selectivity, especially catalyst-controlled site-selectivity.

引用

页码：1092 / 1100

页数：9

共 61 条

[1] Amide Effects in C-H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides [J].

Bisht, Ranjana ;

Hoque, Md Emdadul ;

Chattopadhyay, Buddhadeb .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (48) :15762-15766

[2] Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines [J].

Bisht, Ranjana ;

Chattopadhyay, Buddhadeb .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :84-87

[3] Silyl-directed, iridium-catalyzed ortho-borylation of arenes. A one-pot ortho-borylation of phenols, arylamines, and alkylarenes [J].

Boebel, Timothy A. ;

Hartwig, John. F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (24) :7534-+

[4] Mechanism of the mild functionalization of arenes by diboron reagents catalyzed by iridium complexes. Intermediacy and chemistry of bipyridine-ligated iridium trisboryl complexes [J].

Boller, TM ;

Murphy, JM ;

Hapke, M ;

Ishiyama, T ;

Miyaura, N ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14263-14278

[5] ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].

BROWN, HC ;

COLE, TE .

ORGANOMETALLICS, 1983, 2 (10) :1316-1319

[6] Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions [J].

Chattopadhyay, Buddhadeb ;

Dannatt, Jonathan E. ;

Andujar-De Sanctis, Ivonne L. ;

Gore, Kristin A. ;

Maleczka, Robert E., Jr. ;

Singleton, Daniel A. ;

Smith, Milton R., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) :7864-7871

[7] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[8] meta-Selective C-H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand [J].

Davis, Holly J. ;

Genov, Georgi R. ;

Phipps, Robert J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) :13351-13355

[9] Ion Pair-Directed Regiocontrol in Transition-Metal Catalysis: A Meta-Selective C-H Borylation of Aromatic Quaternary Ammonium Salts [J].

Davis, Holly J. ;

Mihai, Madalina T. ;

Phipps, Robert J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12759-12762

[10] Silyl Phosphorus and Nitrogen Donor Chelates for Homogeneous Ortho Borylation Catalysis [J].

Ghaffari, Behnaz ;

Preshlock, Sean M. ;

Plattner, Donald L. ;

Staples, Richard J. ;

Maligres, Peter E. ;

Krska, Shane W. ;

Maleczka, Robert E., Jr. ;

Smith, Milton R., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14345-14348

← 1 2 3 4 5 6 7 →