Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes

Jørgensen, Kåre B.; Rantanen, Toni; Dörfler, Thilo; Snieckus, Victor

doi:10.1021/acs.joc.5b01300

Cited by 31 publications

(31 citation statements)

References 92 publications

(141 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The right protecting group can serve a double purpose as it can easily be cleaved from the phenanthrene to remove the oxygen left after the DreM reaction. Although the less expensive way of doing this is through a carbamate (25), the more commonly used triflate was used since the cleavage of carbamate inevitably produce a few percent of the alkylated byproduct that would be inseparable from the product by moderate resolution chromatography. The DreM reaction followed by protection with triflic anhydride using 2,6-lutidine as base gave triflates 3a-d in 67-75% yield.…”

Section: Resultsmentioning

confidence: 99%

“…Another main route to the simple substituted phenanthrenes is the combination of directed ortho metalation (DoM), Suzuki-Miyaura cross-coupling and directed remote metalation (DreM) to form phenanthrenes (23). This reaction sequence has been used successfully to make a wide range of substituted phenanthrenes (24,25). Herein, we present a scale-up of the Snieckus route (24) to 4b and 4c and utilize its flexibility to make 4a and 4d.…”

Section: Introductionmentioning

confidence: 99%

“…A more extensive discussion of their applications and synthesis can be found in Wang et al (26) and Jørgensen et al (25).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Regiospecific Synthesis of Dimethylphenanthrenes

Böhme

Lorentzen

Jørgensen

2016

Polycyclic Aromatic Compounds

Self Cite

View full text Add to dashboard Cite

The dimethylated phenanthrenes 2,3-dimethylphenanthrene (4a), 2,7-dimethylphenan threne (4b), 2,6-dimethylphenanthrene (4c) and 1,7-dimethylphenanthrene (4d) have been prepared in gram-quantities by a short sequence of directed ortho metalation (DoM) of N,N-diethylbenzamides followed by Suzuki-Miyaura cross-coupling reaction and directed remote metalation (DreM) to form 9-phenanthrols. The final phenanthrenes were obtained through protection/deprotection as triflates.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Regiospecific Synthesis of Dimethylphenanthrenes

Böhme

Lorentzen

Jørgensen

2016

Polycyclic Aromatic Compounds

Self Cite

View full text Add to dashboard Cite

show abstract

“…These tactics rely on strategically installed metal‐active groups and such starting materials require additional steps to prepare them from feedstock chemical sources. Moreover, harsh reaction conditions are generally needed, thus reducing their versatility and simplicity 10a–d…”

Section: Introductionmentioning

confidence: 99%

Sensitive Amperometric Sensing of Hydrogen Peroxide Using Ag Nanowire Array Electrode

2015

View full text Add to dashboard Cite

A green atom‐economical method for the synthesis of biaryl sulfonamide derivatives via palladium(II)‐catalyzed CH bond activation by employing an amino acid moiety as the bidentate directing group has been developed. The protocol proceeded efficiently in water; high yields and broad substrate scope were achieved. The reaction shows good functional group compatibility and proceeds in a highly selective manner at the ortho position of arenes connected to sulfonamide sulfur atoms. This auxiliary can be easily removed either by acidic hydrolysis, or converted into primary biaryl sulfomamides with a 30 mol % amount of CuO as catalyst. Mechanistic studies show that the present bidentate directing group is essential for promoting ortho CH bond activation of arenes connected to sulfonamide sulfur atoms.

show abstract

“…It was suggested that conditions reported by Jørgensen and Snieckus may be favorable for couplings in the presence of methoxy groups. 88 They noted that when attempting Suzuki reactions on their desired systems with conditions similar to those described above involving Pd(PPh 3 ) 4 , success was limited. Upon exploration of additional conditions, they found that the use of Pd 2 (dba) 3 , SPhos, K 2 PO 4 , and toluene at reflux was more effective for obtaining their desired biaryl products.…”

mentioning

confidence: 99%

Synthesis of potential opioids based on the natural Pawhuskins

Gardner¹

View full text Add to dashboard Cite

Nothing in life is to be feared, it is only to be understood. Now is the time to understand more, so that we may fear less. Marie Curie iii ACKNOWLEDGEMENTS To begin with, this thesis would not be here today if were not for the inspiration, given to me by my professors at Cal Poly Pomona, to continue my education with graduate school. I am incredibly grateful to have had Dr. David Wiemer as an advisor at the University of Iowa, as I value the considerable amount of knowledge and wisdom that he has bestowed on me during my time in graduate school. I cannot thank him enough for his continuous kindness, encouragement, and his extraordinary level of patience, it is truly admirable. Life in the lab would not have been the same without my fellow lab mates past and present. Thank you to Dr. John Kodet and all the other past students who continued to be of assistance beyond their time in the group. Particular thanks should go to Dr. Alyssa Hartung for her guidance when I started my work in the lab and providing several samples for my pawhuskin research, as well as Dr. Jeffrey Neighbors for testing my compounds and his continued collaboration. I would like to thank Carrie Meyers for her assistance in the lab as an undergraduate researcher. For Dr. Veronica Wills, Dr. Rebekah Shippy, and the current students, I am appreciative of all of your support through the new friendships I have formed and for always being there to help solve problems in the lab. The faculty and staff of the Department of Chemistry have been profoundly helpful and supportive throughout my time here in Iowa. I am very grateful for all that they do and for my fellow students in the department who have helped make my graduate iv school experience that much more enjoyable. I would also like to thank the Roy J. Carver Trust for the financial support that allowed me to spend more time in the lab. This journey would have been more trying if it were not for the relentless support and continued encouragement from my parents and the rest of my family. It was always reassuring to know that they were constantly right behind me, cheering me on. Last, but certainly not least, I want to thank my wonderful husband for his constant encouragement and support. Throughout my years in graduate school, he has always been understanding of all the time I have spent in the lab and on my computer at home; and often found ways to help me dedicate even more time towards research. He is incredibly patient, especially when I talk endlessly about chemistry. I have always enjoyed his take on what I do; even when he constantly reminds me that a geranyl chain resembles a staircase. Thank you, Joe, for being one of my biggest supporters, and always finding ways to bring laughter into every single one of my days.

show abstract

Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes

Cited by 31 publications

References 92 publications

Regiospecific Synthesis of Dimethylphenanthrenes

Regiospecific Synthesis of Dimethylphenanthrenes

Sensitive Amperometric Sensing of Hydrogen Peroxide Using Ag Nanowire Array Electrode

Synthesis of potential opioids based on the natural Pawhuskins

Contact Info

Product

Resources

About