Mechanistic Insights into Two-Phase Radical C-H Arylations

被引：31

作者：

Baxter, Ryan D. ^{[1
]}

Liang, Yong ^{[2
]}

Hong, Xin ^{[2
]}

Brown, Timothy A. ^{[3
]}

Zare, Richard N. ^{[3
]}

Houk, K. N. ^{[2
]}

Baran, Phil S. ^{[1
]}

Blackmond, Donna G. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[3] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ACS CENTRAL SCIENCE | 2015年 / 1卷 / 08期

基金：

美国国家科学基金会;

关键词：

ELECTRON-DEFICIENT HETEROCYCLES; ARYLBORONIC ACIDS; MASS; SUBSTITUTIONS; HETEROARENES;

D O I：

10.1021/acscentsci.5b00332

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Kinetic, spectroscopic, and computational studies of radical C-H arylations highlight the interplay between chemical and physical rate processes in these multiphase reactions. Anomalous concentration dependences observed here may be reconciled by considering the role of phase transfer processes that mediate concentrations in each phase. In addition, understanding interactions through phase boundaries enables their use in optimization of reaction performance.

引用

页码：456 / 462

页数：7

共 31 条

[1]

Baumann E., 1886, Ber. Dtsch. Chem. Ges, V19, P3218, DOI [10.1002/cber.188601902348, DOI 10.1002/CBER.188601902348]

[2] Transition Metal-Mediated Direct C-H Arylation of Heteroarenes Involving Aryl Radicals [J].

Bonin, Helene ;

Sauthier, Mathieu ;

Felpin, Francois-Xavier .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :645-671

[3] Size-Controlled Flow Synthesis of Gold Nanoparticles Using a Segmented Flow Microfluidic Platform [J].

Cabeza, Victor Sebastian ;

Kuhn, Simon ;

Kulkarni, Amol A. ;

Jensen, Klavs F. .

LANGMUIR, 2012, 28 (17) :7007-7013

[4] Iron-Catalyzed Direct C-H Arylation of Heterocycles and Quinones with Arylboronic Acids [J].

Deb, Arghya ;

Manna, Srimanta ;

Maji, Arun ;

Dutta, Uttam ;

Maiti, Debabrata .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) :5251-5256

[5] Silver-Catalyzed Direct C-H Arylation of N-Iminopyridinium Ylides with Arylboronic Acids [J].

Fang, Lei ;

Shi, Xiaoyun ;

Chen, Liangshun ;

Yu, Jianjun ;

Wang, Limin .

SYNLETT, 2014, 25 (10) :1413-1418

[6] Practical C-H Functionalization of Quinones with Boronic Acids [J].

Fujiwara, Yuta ;

Domingo, Victoriano ;

Seiple, Ian B. ;

Gianatassio, Ryan ;

Del Bel, Matthew ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3292-3295

[7] Detection of transient radical cations in electron transfer-initiated Diels-Alder reactions by electrospray ionization mass spectrometry [J].

Fürmeier, S ;

Metzger, JO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (44) :14485-14492

[8]

Harrowven DC, 2004, PROG HET CH, V16, P27

[9] The direct arylation of benzoquinones with arylboronic acid promoted by iron(II) oxalate [J].

Huang, Yibo ;

Guan, Dan .

JOURNAL OF CHEMICAL RESEARCH, 2013, (11) :649-651

[10] Trinuclear Pd3O2 Intermediate in Aerobic Oxidation Catalysis [J].

Ingram, Andrew J. ;

Solis-Ibarra, Diego ;

Zare, Richard N. ;

Waymouth, Robert M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) :5648-5652

← 1 2 3 4 →