Alcohol-alcohol cross-coupling enabled by SH2 radical sorting

被引:58
作者
Chen, Ruizhe [1 ]
Intermaggio, Nicholas E. [1 ]
Xie, Jiaxin [1 ]
Rossi-Ashton, James A. [1 ]
Gould, Colin A. [1 ]
Martin, Robert T. [1 ]
Alcazar, Jesus [2 ]
MacMillan, David W. C. [1 ]
机构
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
[2] Janssen Cilag SA, Discovery Chem, Janssen Res & Dev, C Jarama 75A, Toledo 45007, Spain
基金
美国国家科学基金会;
关键词
BOND-DISSOCIATION; MECHANISM;
D O I
10.1126/science.adl5890
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
Alcohols represent a functional group class with unparalleled abundance and structural diversity. In an era of chemical synthesis that prioritizes reducing time to target and maximizing exploration of chemical space, harnessing these building blocks for carbon-carbon bond-forming reactions is a key goal in organic chemistry. In particular, leveraging a single activation mode to form a new C(sp(3))-C(sp(3)) bond from two alcohol subunits would enable access to an extraordinary level of structural diversity. In this work, we report a nickel radical sorting-mediated cross-alcohol coupling wherein two alcohol fragments are deoxygenated and coupled in one reaction vessel, open to air.
引用
收藏
页码:1350 / 1357
页数:8
相关论文
共 62 条
[31]   Overcoming the limitations of Kolbe coupling with waveform-controlled electrosynthesis [J].
Hioki, Yuta ;
Costantini, Matteo ;
Griffin, Jeremy ;
Harper, Kaid C. ;
Merini, Melania Prado ;
Nissl, Benedikt ;
Kawamata, Yu ;
Baran, Phil S. .
SCIENCE, 2023, 380 (6640) :81-87
[32]  
Holson E., 2016, International Patent Application Publication, Patent No. [2016/100940A1, 2016100940]
[33]   O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols [J].
Jeffrey, Jenna L. ;
Terrett, Jack A. ;
MacMillan, David W. C. .
SCIENCE, 2015, 349 (6255) :1532-1536
[34]   EXPERIMENTAL CORRECTION FOR THE INNER-FILTER EFFECT IN FLUORESCENCE-SPECTRA [J].
KUBISTA, M ;
SJOBACK, R ;
ERIKSSON, S ;
ALBINSSON, B .
ANALYST, 1994, 119 (03) :417-419
[35]   Decarboxylative Cross-Coupling: A Radical Tool in Medicinal Chemistry [J].
Laudadio, Gabriele ;
Palkowitz, Maximilian D. ;
Ewing, Tamara El-Hayek ;
Baran, Phil S. .
ACS MEDICINAL CHEMISTRY LETTERS, 2022, 13 (09) :1413-1420
[36]   Selective sp3 C-H alkylation via polarity-match-based cross-coupling [J].
Le, Chip ;
Liang, Yufan ;
Evans, Ryan W. ;
Li, Ximing ;
MacMillan, David W. C. .
NATURE, 2017, 547 (7661) :79-83
[37]   Carbon-centered radical capture at nickel(II) complexes: Spectroscopic evidence, rates, and selectivity [J].
Lin, Qiao ;
Spielvogel, Ethan H. ;
Diao, Tianning .
CHEM, 2023, 9 (05) :1295-1308
[38]   A biomimetic SH2 cross-coupling mechanism for quaternary sp3-carbon formation [J].
Liu, Wei ;
Lavagnino, Marissa N. ;
Gould, Colin A. ;
Alcazar, Jesus ;
MacMillan, David W. C. .
SCIENCE, 2021, 374 (6572) :1259-+
[39]   Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success [J].
Lovering, Frank ;
Bikker, Jack ;
Humblet, Christine .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (21) :6752-6756
[40]   Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex [J].
Lowry, MS ;
Goldsmith, JI ;
Slinker, JD ;
Rohl, R ;
Pascal, RA ;
Malliaras, GG ;
Bernhard, S .
CHEMISTRY OF MATERIALS, 2005, 17 (23) :5712-5719