High-throughput photocapture approach for reaction discovery

被引:50
作者
Bayly, Alison A. [1 ]
McDonald, Benjamin R. [1 ]
Mrksich, Milan [1 ]
Scheidt, Karl A. [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
high-throughput analysis; self-assembled monolayers; photocapture; azoliums; MASS-SPECTROMETRY; PHOTOREDOX CATALYSIS; RADICAL REACTIONS; LIGHT; OXIDATION; ALDEHYDES;
D O I
10.1073/pnas.2003347117
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Modern organic reaction discovery and development relies on the rapid assessment of large arrays of hypothesis-driven experiments. The time-intensive nature of reaction analysis presents the greatest practical barrier for the execution of this iterative process that underpins the development of new bioactive agents. Toward addressing this critical bottleneck, we report herein a high-throughput analysis (HTA) method of reaction mixtures by photocapture on a 384-spot diazirine-terminated self-assembled monolayer, and self-assembled monolayers for matrix-assisted laser desorption/ionization mass spectrometry (SAMDI-MS) analysis. This analytical platform has been applied to the identification of a single-electron-promoted reductive coupling of acyl azolium species.
引用
收藏
页码:13261 / 13266
页数:6
相关论文
共 38 条
[21]   Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity [J].
McNally, Andrew ;
Prier, Christopher K. ;
MacMillan, David W. C. .
SCIENCE, 2011, 334 (6059) :1114-1117
[22]   Mass spectrometry of self-assembled monolayers: A new tool for molecular surface science [J].
Mrksich, Milan .
ACS NANO, 2008, 2 (01) :7-18
[23]   Visible light photoredox catalysis: applications in organic synthesis [J].
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :102-113
[24]   Electrochemical Characterization of Azolium Salts [J].
Ogawa, Kelli A. ;
Boydston, Andrew J. .
CHEMISTRY LETTERS, 2014, 43 (06) :907-909
[25]   Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis [J].
Patel, Niki R. ;
Kelly, Christopher B. ;
Jouffroy, Matthieu ;
Molander, Gary A. .
ORGANIC LETTERS, 2016, 18 (04) :764-767
[26]   Photogenerated acyl/alkoxycarbonyl/carbamoyl radicals for sustainable synthesis [J].
Raviola, Carlotta ;
Protti, Stefano ;
Ravelli, Davide ;
Fagnoni, Maurizio .
GREEN CHEMISTRY, 2019, 21 (04) :748-764
[27]   A Simple, Multidimensional Approach to High-Throughput Discovery of Catalytic Reactions [J].
Robbins, Daniel W. ;
Hartwig, John F. .
SCIENCE, 2011, 333 (6048) :1423-1427
[28]   Nanomole-scale high-throughput chemistry for the synthesis of complex molecules [J].
Santanilla, Alexander Buitrago ;
Regalado, Erik L. ;
Pereira, Tony ;
Shevlin, Michael ;
Bateman, Kevin ;
Campeau, Louis-Charles ;
Schneeweis, Jonathan ;
Berritt, Simon ;
Shi, Zhi-Cai ;
Nantermet, Philippe ;
Liu, Yong ;
Helmy, Roy ;
Welch, Christopher J. ;
Vachal, Petr ;
Davies, Ian W. ;
Cernak, Tim ;
Dreher, Spencer D. .
SCIENCE, 2015, 347 (6217) :49-53
[29]   Photoredox Catalysis in Organic Chemistry [J].
Shaw, Megan H. ;
Twilton, Jack ;
MacMillan, David W. C. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6898-6926
[30]   Novel Acoustic Loading of a Mass Spectrometer: Toward Next-Generation High-Throughput MS Screening [J].
Sinclair, Ian ;
Stearns, Rick ;
Pringle, Steven ;
Wingfield, Jonathan ;
Datwani, Sammy ;
Hall, Eric ;
Ghislain, Luke ;
Majlof, Lars ;
Bachman, Martin .
JALA, 2016, 21 (01) :19-26