Palladium catalyzed/silver tuned selective mono-/tetra-acetoxylation of o-carboranes via B-H activation

被引：77

作者：

Cao, Ke ^{[1
]}

Xu, Tao-Tao

Wu, Ji

Jiang, Linhai

Yang, Junxiao

机构：

[1] Southwest Univ Sci & Technol Mianyang, State Key Lab Cultivat Base Nonmet Composite & Fu, Mianyang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 76期

关键词：

BORON CLUSTERS; SILVER SALT; CHEMISTRY; BONDS; HYDROXYLATION; COORDINATION; METATHESIS; COMPLEXES; LIGAND;

D O I：

10.1039/c6cc06200h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium catalyzed/silver tuned selective mono- and tetra-acetoxylation of o-carboranes has been developed, and a series of mono- and tetra-acetoxylated o-carboranes decorated with active groups have been synthesized with moderate to good yields as well as excellent selectivity. A mechanism involving electrophilic palladation and cyclopalladation of the B-H bond was proposed.

引用

页码：11446 / 11449

页数：4

共 51 条

[1] 9-IODO-ORTHO-CARBORANE [J].

ANDREWS, JS ;

ZAYAS, J ;

JONES, M .

INORGANIC CHEMISTRY, 1985, 24 (22) :3715-3716

[2] DICARBA-CLOSO-DODECABORANES C2B10H12 AND THEIR DERIVATIVES [J].

BREGADZE, VI .

CHEMICAL REVIEWS, 1992, 92 (02) :209-223

[3] Palladium catalyzed selective mono-arylation of o-carboranes via B-H activation [J].

Cao, Ke ;

Huang, Yawen ;

Yang, Junxiao ;

Wu, Ji .

CHEMICAL COMMUNICATIONS, 2015, 51 (33) :7257-7260

[4] Synthesis and Properties of Carborane-Appended C3-Symmetrical Extended π Systems [J].

Dash, Barada Prasanna ;

Satapathy, Rashmirekha ;

Gaillard, Elizabeth R. ;

Maguire, John A. ;

Hosmane, Narayan S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (18) :6578-6587

[5] Advances in the chemistry of carboranes and metallacarboranes with more than 12 vertices [J].

Deng, Liang ;

Xie, Zuowei .

COORDINATION CHEMISTRY REVIEWS, 2007, 251 (17-20) :2452-2476

[6] B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes [J].

Dziedzic, Rafal M. ;

Saleh, Liban M. A. ;

Axtell, Jonathan C. ;

Martin, Joshua L. ;

Stevens, Simone L. ;

Royappa, A. Timothy ;

Rheingold, Arnold L. ;

Spokoyny, Alexander M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (29) :9081-9084

[7]

Grimes RN, 2011, CARBORANES, 2ND EDITION, P1

[8] Synthesis, structure, and reactivity of closo-2,3,4,5,6,7,8,9,10,11-decahydroxy-1,12-bis(sulfonic acid)-1,12-dicarbadodecaborane(12) [J].

Herzog, A ;

Knobler, CB ;

Hawthorne, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12791-12797

[9]

Hosmane N.S., 2007, COMPREHENSIVE ORGANO, P175, DOI DOI 10.1016/B0-08-045047-4/00046-7

[10]

Hosmane NS, 2012, BORON SCIENCE: NEW TECHNOLOGIES AND APPLICATIONS, P1

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