Additive- and Metal-Free, Predictably 1,2-and 1,3-Regioselective, Photoinduced Dual C-H/C-X Borylation of Haloarenes

被引：114

作者：

Mfuh, Adelphe M. ^{[1
]}

Nguyen, Vu T. ^{[1
]}

Chhetri, Bhuwan ^{[1
]}

Burch, Jessica E. ^{[1
]}

Doyle, John D. ^{[1
]}

Nesterov, Vladimir N. ^{[2
]}

Arman, Hadi D. ^{[1
]}

Larionov, Oleg V. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

[2] Univ North Texas, Dept Chem, Denton, TX 76201 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 27期

关键词：

CATALYZED CROSS-COUPLINGS; ARYL HALIDES; BUILDING-BLOCKS; H BORYLATION; SOLVENT; NUCLEOPHILES; REACTIVITY; BENZENES; SUBSTITUTION; TEMPERATURE;

D O I：

10.1021/jacs.6b05436

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein a simple, additive- and metal-free, photoinduced, dual C-H/C-X borylation of chloro-, bromo-, and iodoarenes. The reaction produces 1,2- and 1,3-diborylarenes on gram scales under batch and continuous flow conditions. The regioselectivity of the dual C-H/C-X borylation is determined by the solvent and the substituents in the parent haloarenes.

引用

页码：8408 / 8411

页数：4

共 64 条

[1] Zinc-Catalyzed Dual C-X and C-H Borylation of Aryl Halides [J].

Bose, Shubhankar Kumar ;

Deissenberger, Andrea ;

Eichhorn, Antonius ;

Steel, Patrick G. ;

Lin, Zhenyang ;

Marder, Todd B. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (40) :11843-11847

[2] A leap ahead for activating C-H bonds [J].

Bose, Shubhankar Kumar ;

Marder, Todd B. .

SCIENCE, 2015, 349 (6247) :473-474

[3] Efficient Synthesis of Aryl Boronates via Zinc-Catalyzed Cross-Coupling of Alkoxy Diboron Reagents with Aryl Halides at Room Temperature [J].

Bose, Shubhankar Kumar ;

Marder, Todd B. .

ORGANIC LETTERS, 2014, 16 (17) :4562-4565

[4] Solvent cage effects. I. Effect of radical mass and size on radical cage pair recombination efficiency. II. Is geminate recombination of polar radicals sensitive to solvent polarity? [J].

Braden, DA ;

Parrack, EE ;

Tyler, DR .

COORDINATION CHEMISTRY REVIEWS, 2001, 211 :279-294

[5] ORGANIC SYNTHESES VIA FREE-RADICAL DISPLACEMENT REACTIONS OF ORGANOBORANES [J].

BROWN, HC ;

MIDLAND, MM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (08) :692-&

[6] AROMATIC-SUBSTITUTION BY SRN1 MECHANISM [J].

BUNNETT, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (11) :413-420

[7] Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions [J].

Chen, Kai ;

Cheung, Man Sing ;

Lin, Zhenyang ;

Li, Pengfei .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (07) :875-879

[8] Synthesis of aryl trimethylstannanes from aryl halides: an efficient photochemical method [J].

Chen, Kai ;

He, Pei ;

Zhang, Shuai ;

Li, Pengfei .

CHEMICAL COMMUNICATIONS, 2016, 52 (58) :9125-9128

[9] Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions [J].

Chen, Kai ;

Zhang, Shuai ;

He, Pei ;

Li, Pengfei .

CHEMICAL SCIENCE, 2016, 7 (06) :3676-3680

[10] 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

← 1 2 3 4 5 6 7 →