Adual light-driven palladium catalyst: Breaking the barriers incarbonylation reactions

被引:202
作者
Torres, Gerardo M. [1 ]
Liu, Yi [1 ]
Arndtsen, Bruce A. [1 ]
机构
[1] McGill Univ, Dept Chem, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
ALKYL IODIDES; HECK REACTION; PHOTOREDOX; CARBONYLATION; RADICALS; COMPLEXES; CHEMISTRY; ALDEHYDES; CO; FUNCTIONALIZATION;
D O I
10.1126/science.aba5901
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
Transition metal-catalyzed coupling reactions have become one of the most important tools in modern synthesis. However, an inherent limitation to these reactions is the need to balance operations, because the factors that favor bond cleavage via oxidative addition ultimately inhibit bond formation via reductive elimination. Here, we describe an alternative strategy that exploits simple visible-light excitation of palladium to drive both oxidative addition and reductive elimination with low barriers. Palladium-catalyzed carbonylations can thereby proceed under ambient conditions, with challenging aryl or alkyl halides and difficult nucleophiles, and generate valuable carbonyl derivatives such as acid chlorides, esters, amides, or ketones in a now-versatile fashion. Mechanistic studies suggest that concurrent excitation of palladium(O) and palladium(II) intermediates is responsible for this activity.
引用
收藏
页码:318 / +
页数:187
相关论文
共 88 条
  • [41] Li G., 2014, Guangzhou Chemical Industry, V20, P91
  • [42] Palladium-imidazolium N-heterocyclic carbene-catalyzed carbonylative amidation with boronic acids, aryl diazonium ions, and ammonia
    Ma, YD
    Song, C
    Chai, Q
    Ma, CQ
    Andrus, MB
    [J]. SYNTHESIS-STUTTGART, 2003, (18): : 2886 - 2889
  • [43] Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis
    Macias, Maximiliano De La Higuera
    Arndtsen, Bruce A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) : 10140 - 10144
  • [44] Palladium-catalyzed aminocarbonylation of aryl chlorides at atmospheric pressure: The dual role of sodium phenoxide
    Martinelli, Joseph R.
    Clark, Thomas P.
    Watson, Donald A.
    Munday, Rachel H.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) : 8460 - 8463
  • [45] Fenofibrate A Review of its Use in Dyslipidaemia
    McKeage, Kate
    Keating, Gillian M.
    [J]. DRUGS, 2011, 71 (14) : 1917 - 1946
  • [46] The Challenge of Palladium-Catalyzed Aromatic Azidocarbonylation: From Mechanistic and Catalyst Deactivation Studies to a Highly Efficient Process
    Miloserdov, Fedor M.
    McMullin, Claire L.
    Martinez Belmonte, Marta
    Benet-Buchholz, Jordi
    Bakhmutov, Vladimir I.
    Macgregor, Stuart A.
    Grushin, Vladimir V.
    [J]. ORGANOMETALLICS, 2014, 33 (03) : 736 - 752
  • [47] Microwave-Assisted Synthesis of Heteroleptic Ir(III)+ Polypyridyl Complexes
    Monos, Timothy M.
    Sun, Alexandra C.
    McAtee, Rory C.
    Devery, James J., III
    Stephenson, Corey R. J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) : 6988 - 6994
  • [48] Amide bond formation and peptide coupling
    Montalbetti, CAGN
    Falque, V
    [J]. TETRAHEDRON, 2005, 61 (46) : 10827 - 10852
  • [49] Mori N., 2004, SYNLETT, V2004
  • [50] Photo-activation of Pd-catalyzed Sonogashira coupling using a Ru/bipyridine complex as energy transfer agent
    Osawa, Masahisa
    Nagai, Hidetada
    Akita, Munetaka
    [J]. DALTON TRANSACTIONS, 2007, (08) : 827 - 829