Green photochemistry: Production of fine chemicals with sunlight

Oelgemöller, Michael; Jung, Christian; Mattay, Jochen

doi:10.1351/pac200779111939

Cited by 156 publications

(76 citation statements)

References 77 publications

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“…Light is a clean and highly selective reagent that can be readily controlled and dosed. Photochemical and photocatalytic key-steps are therefore more and more recognized as a powerful extension of conventional methods in organic synthesis [46][47][48][49][50][51][52]. This current trend of green and solar photochemistry will certainly be further strengthened in the next decades by the advent of continuous flow (micro)reactors as a new tool for more efficient photochemical synthesis [53][54][55], and by the gradual progress achieved in light-induced enantioselective catalysis, asymmetric photochemistry and photochirogenesis [56][57][58].…”

Section: Artificial Photoenzymes In Green Chemistry and Synthesismentioning

confidence: 99%

The concept of photochemical enzyme models – State of the art

Knör

2016

Coordination Chemistry Reviews

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Section: Artificial Photoenzymes In Green Chemistry and Synthesismentioning

confidence: 99%

The concept of photochemical enzyme models – State of the art

Knör

2016

Coordination Chemistry Reviews

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“…Using photoreactors in Germany, researchers have carried out photoacylation and photooxygenations, producing important synthetic intermediates and commercial fragrances in bulk with minimal consumption of fossil energy. 82 Another example of the energy savings that can be realized by harnessing sunlight or artificial UV light is photocurable resins: BASF has developed automotive primer coatings that crosslink readily under light irradiation. The new coatings obviate the need for energy-intensive bake ovens used to thermally cure conventional primers.…”

Section: Energy Impactsmentioning

confidence: 99%

Green Chemistry: A design framework for sustainability

Beach

Cui

Anastas

2009

Energy Environ. Sci.

206

100

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In this review we will highlight some of the science that exemplifies the principles of Green Chemistry, in particular the efficient use of materials and energy, development of renewable resources, and design for reduced hazard. Examples are drawn from a diverse range of research fields including catalysis, alternative solvents, analytical chemistry, polymer science, and toxicology. While it is impossible for us to be comprehensive, as the worldwide proliferation of Green Chemistry research, industrial application, conferences, networks, and journals has led to a wealth of innovation, the review will attempt to illustrate how progress has been made toward solving the sustainability goals of the 21st century by engaging at the molecular level.

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“…[44] The reaction was also applicable to simpler iodoallylamines as shown for the diethylamine analogue (Scheme 9). However, the synthetic value of this newly found photooxidation remains limited, as the b-aminoacroleine products are also available from the simple 1,4-addition of amines to propiolaldehyde.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Meloscine by a [2+2]‐Photocycloaddition/Ring‐Expansion Route

Selig

Herdtweck

Bach

2009

Chemistry A European J

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The unusual monoterpenoid indole alkaloid meloscine was synthesized starting from a protected aminoethylquinolone in 15 steps and an overall yield of 9%, employing a [2+2]-photocycloaddition as the stereochemistry defining key step. After the initial plan of a Wagner-Meerwein type rearrangement of a [4.2.0]- into a [3.3.0]-bicyclic substructure could not be realized, the required ring enlargement of a cyclobutane was eventually achieved by a retro-benzilic acid rearrangement. Generation of the central pyrrolidine ring was possible by a three-step reductive amination domino sequence. The final ring was built up by a ring-closing metathesis after the last quaternary stereocenter had been constructed by a Johnson-Claisen rearrangement. The synthesis was concluded by a selenylation-elimination sequence to build up the exocyclic vinyl group of meloscine. Using our methodology for enantioselective [2+2]-photocycloaddition mediated by a chiral complexation agent, the experimentally very simple synthesis could be performed in an enantioselective fashion (7 % overall yield). The enantioselective synthesis of (+)-meloscine represents the first example of a natural product synthesis employing an enantioselective [2+2]-photocycloaddition as its key step, and illustrates nicely the synthetic potential of photochemical transformations for the construction of complex heterocyclic structures.

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Green photochemistry: Production of fine chemicals with sunlight

Cited by 156 publications

References 77 publications

The concept of photochemical enzyme models – State of the art

The concept of photochemical enzyme models – State of the art

Green Chemistry: A design framework for sustainability

Total Synthesis of Meloscine by a [2+2]‐Photocycloaddition/Ring‐Expansion Route

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