@article{SchmidtRiemerSchilde2014, author = {Schmidt, Bernd and Riemer, Martin and Schilde, Uwe}, title = {Chroman-4-ones via microwave-promoted domino claisen rearrangement-oxa-michael addition: Synthesis of tabchromones A and B}, series = {Synlett : accounts and rapid communications in synthetic organic chemistry}, volume = {25}, journal = {Synlett : accounts and rapid communications in synthetic organic chemistry}, number = {20}, publisher = {Thieme}, address = {Stuttgart}, issn = {0936-5214}, doi = {10.1055/s-0034-1379364}, pages = {2943 -- 2946}, year = {2014}, abstract = {Allyl phenyl ethers with a pendant enone substituent undergo, upon microwave irradiation, a domino sequence of Claisen rearrangement and 6-endo-trig-cyclization to furnish functionalized chroman-4-ones. The natural products tabchromones A and B were synthesized via this method.}, language = {en} } @article{SchmidtRiemerSchilde2015, author = {Schmidt, Bernd and Riemer, Martin and Schilde, Uwe}, title = {Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {34}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201501151}, pages = {7602 -- 7611}, year = {2015}, abstract = {Allyl, dimethylallyl and prenyl ethers derived from o-acyl-phenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.}, language = {en} } @article{SchmidtRiemerKarras2013, author = {Schmidt, Bernd and Riemer, Martin and Karras, Manfred}, title = {2,2 '-Biphenols via protecting group-free thermal or microwave-accelerated suzuki-miyaura coupling in water}, series = {The journal of organic chemistry}, volume = {78}, journal = {The journal of organic chemistry}, number = {17}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo401398n}, pages = {8680 -- 8688}, year = {2013}, abstract = {User-friendly protocols for the protecting group-free synthesis of 2,2'-biphenols via Suzuki-Miyaura coupling of o-halophenols and o-boronophenol are presented. The reactions proceed in water in the presence of simple additives such as K2CO3, KOH, KF, or TBAF and with commercially available Pd/C as precatalyst. Expensive or laboriously synthesized ligands or other additives are not required. In the case of bromophenols, efficient rate acceleration and short reaction times were accomplished by microwave irradiation.}, language = {en} } @article{SchmidtRiemer2015, author = {Schmidt, Bernd and Riemer, Martin}, title = {Synthesis of Magnaldehydes B and E and Dictyobiphenyl B by Microwave-Promoted Cross-Coupling of Boronophenols}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, number = {17}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201500350}, pages = {3760 -- 3766}, year = {2015}, abstract = {Magnaldehydes B and E along with their 4'-methylated derivatives are naturally occurring 2,4'-biphenols that have been isolated from the Magnoliaceae. Herein, these natural products have been synthesized from a common intermediate, which was obtained by a microwave-promoted, hetero-geneously catalyzed, and protecting-group-free Suzuki-Miyaura coupling reaction in an aqueous medium. These reaction conditions were also successfully applied to a one-step synthesis of the slime mold metabolite dictyobiphenyl B.}, language = {en} } @article{SchmidtRiemer2014, author = {Schmidt, Bernd and Riemer, Martin}, title = {Suzuki-Miyaura coupling of halophenols and phenol boronic acids: systematic investigation of positional isomer effects and conclusions for the synthesis of phytoalexins from Pyrinae}, series = {The journal of organic chemistry}, volume = {79}, journal = {The journal of organic chemistry}, number = {9}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo500675a}, pages = {4104 -- 4118}, year = {2014}, abstract = {The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.}, language = {en} } @article{SchmidtRiemer2016, author = {Schmidt, Bernd and Riemer, Martin}, title = {Microwave-Promoted Deprenylation: Prenyl Ether as a Thermolabile Phenol Protecting Group}, series = {Synthesis}, volume = {48}, journal = {Synthesis}, publisher = {Thieme}, address = {Stuttgart}, issn = {0039-7881}, doi = {10.1055/s-0035-1561366}, pages = {1399 -- 1406}, year = {2016}, abstract = {para-Substituted aryl prenyl ethers undergo a deprenylation reaction upon microwave irradiation. This offers the opportunity to use a prenyl ether as a thermolabile protecting group in the synthesis of natural products with a chromone structure, which proceeds via a tandem deprenylation/6-endo-cyclization sequence.}, language = {en} } @article{SchmidtRiemer2016, author = {Schmidt, Bernd and Riemer, Martin}, title = {Synthesis of Allyl- and Prenylcoumarins via Microwave-Promoted Tandem Claisen Rearrangement/Wittig Olefination}, series = {Synthesis}, volume = {48}, journal = {Synthesis}, publisher = {Thieme}, address = {Stuttgart}, issn = {0039-7881}, doi = {10.1055/s-0035-1560501}, pages = {141 -- 149}, year = {2016}, abstract = {Allyl, dimethylallyl, crotyl, and prenyl ethers of various aromatic ortho-hydroxy carbonyl compounds undergo a tandem sequence of Claisen rearrangement, carbonyl olefination, and cyclization upon microwave irradiation in the presence of a stabilized ylide. The products are multiply substituted 6- or 8-allylated or prenylated coumarins (2H-chromen-2-ones).}, language = {en} } @article{SchmidtRiemer2017, author = {Schmidt, Bernd and Riemer, Martin}, title = {Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols}, series = {Journal of Heterocyclic Chemistry}, volume = {54}, journal = {Journal of Heterocyclic Chemistry}, number = {2}, publisher = {Wiley}, address = {Hoboken}, issn = {0022-152X}, doi = {10.1002/jhet.2704}, pages = {1287 -- 1297}, year = {2017}, abstract = {ortho-Aryl phenols, synthesized via protecting group free Suzuki-Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C-H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)(2) without additional ligands.}, language = {en} } @article{RiemerRiemerKruegeretal.2021, author = {Riemer, Nastja and Riemer, Martin and Kr{\"u}ger, Mandy and Clarkson, Guy J. and Shipman, Michael and Schmidt, Bernd}, title = {Synthesis of arylidene-beta-lactams via exo-selective Matsuda-Heck arylation of methylene-beta-lactams}, series = {The journal of organic chemistry : JOC}, volume = {86}, journal = {The journal of organic chemistry : JOC}, number = {13}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/acs.joc.1c00638}, pages = {8786 -- 8796}, year = {2021}, abstract = {exo-Methylene-beta-lactams were synthesized in two steps from commercially available 3-bromo-2-(bromomethyl)-propionic acid and reacted with arene diazonium salts in a Heck-type arylation in the presence of catalytic amounts of Pd(OAc)(2) under ligand-free conditions. The products, arylidene-beta-lactams, were obtained in high yields as single isomers. The beta-hydride elimination step of the Pd-catalyzed coupling reaction proceeds with high exo-regioselectivity and E-stereoselectivity. With aryl iodides, triflates, or bromides, the coupling products were isolated only in low yields, due to extensive decomposition of the starting material at elevated temperatures. This underlines that arene diazonium salts can be superior arylating reagents in Heck-type reactions and yield coupling products in synthetically useful yields and selectivities when conventional conditions fail.}, language = {en} }