Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C-H Activation with Silyldimesitylborane

被引：7

作者：

Shishido, Ryosuke ^{[1
]}

Sasaki, Ikuo ^{[2
]}

Seki, Tomohiro ^{[1
,3
]}

Ishiyama, Tatsuo ^{[1
]}

Ito, Hajime ^{[1
,3
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Appl Chem, Kita Ku, Kita 13 Nishi 8, Sapporo, Hokkaido 0608628, Japan

[2] Aoyama Gakuin Univ, Fac Sci & Technol, Dept Chem & Biosci, Chuo Ku, 5-10-1 Fuchinobe, Sagamihara, Kanagawa 2525258, Japan

[3] Hokkaido Univ, Inst Chem React Design & Discovery WPI ICRD, Kita Ku, Kita 21,Nishi 10, Sapporo, Hokkaido 0010021, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 56期

关键词：

benzofuran; C-H borylation; dimesitylboryl group; iridium catalyst; silyldimesitylborane; TRIVALENT BORON; BOND ACTIVATION; SINGLE-PHOTON; BORYLATION; MECHANISM; ACCEPTOR; ARENES; COMPLEXES; DONOR; BULKY;

D O I：

10.1002/chem.201903776

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct dimesitylborylation of benzofuran derivatives by a C-H activation catalyzed by an iridium(I)/N-heterocyclic carbene (NHC) complex in the presence of Ph2MeSi-BMes(2) afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. This method provides a straightforward route to donor-(pi-spacer)-acceptor systems with intriguing solvatochromic luminescence properties.

引用

页码：12924 / 12928

页数：5

共 50 条

[41] Iridium-Catalyzed Phosphoramidation of Arene C-H Bonds with Phosphoryl Azide
Pan, Changduo
Jin, Ning
Zhang, Honglin
Han, Jie
Zhu, Chengjian
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9427 - 9432
[42] Iridium-Catalyzed Direct C-H Amination with Alkylamines: Facile Oxidative Insertion of Amino Group into Iridacycle
Kim, Hyunwoo
Chang, Sukbok
ACS CATALYSIS, 2015, 5 (11): : 6665 - 6669
[43] Iridium-Catalyzed Direct Hydroarylation of Glycals via C-H Activation: Ligand-Controlled Stereoselective Synthesis of α- and β-C-Glycosyl Arenes
Sakamoto, Kana
Nagai, Masaki
Ebe, Yusuke
Yorimitsu, Hideki
Nishimura, Takahiro
ACS CATALYSIS, 2019, 9 (02) : 1347 - 1352
[44] Iridium-Catalyzed C-H Activation versus Directed ortho Metalation: Complementary Borylation of Aromatics and Heteroaromatics
Hurst, Timothy E.
Macklin, Todd K.
Becker, Maike
Hartmann, Eduard
Kuegel, Wolfgang
Parisienne-La Salle, Jean-Christophe
Batsanov, Andrei S.
Marder, Todd B.
Snieckus, Victor
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8155 - 8161
[45] Iridium-Catalyzed Arene Ortho-Silylation by Formal Hydroxyl-Directed C-H Activation
Simmons, Eric M.
Hartwig, John F.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (48) : 17092 - 17095
[46] Iridium-Catalyzed Branch-Selective Hydroarylation of Vinyl Ethers via C-H Bond Activation
Ebe, Yusuke
Nishimura, Takahiro
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (18) : 5899 - 5902
[47] Iridium-Catalyzed Direct C-H Amidation Polymerization: Step-Growth Polymerization by C-N Bond Formation via C-H Activation to Give Fluorescent Polysulfonamides
Jang, Yoon-Jung
Hwang, Soon-Hyeok
Choi, Tae-Lim
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (46) : 14474 - 14478
[48] Recent Advances in Iridium-Catalyzed Alkylation of C-H and N-H Bonds
Pan, Shiguang
Shibata, Takanori
ACS CATALYSIS, 2013, 3 (04): : 704 - 712
[49] Tail-To-Tail Stereoselective Dimerization of Acrylate Derivatives via Iridium-Catalyzed Vinylic sp2 C-H Activation
Kojima, Masafumi
Sasaki, Mio
Ito, Mamoru
Shibata, Takanori
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (10) : 1666 - 1670
[50] Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C-H Functionalization
Fischer, Daniel F.
Sarpong, Richmond
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 5926 - +

← 1 2 3 4 5 →