Christopher J Douglas

19992020

Research output per year

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Research Output

  • 51 Article
  • 2 Comment/debate
  • 1 Conference contribution
  • 1 Review article
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Article
2020

Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments

Pound, S. M., Underwood, S. J. & Douglas, C. J., Jan 1 2020, (Accepted/In press) In : European Journal of Organic Chemistry.

Research output: Contribution to journalArticle

2019

Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene

Frost, G. B., Mittelstaedt, M. N. & Douglas, C. J., Feb 1 2019, In : Chemistry - A European Journal. 25, 7, p. 1727-1732 6 p.

Research output: Contribution to journalArticle

1 Scopus citations

Preparation of bis-Benzyne Precursor 2,5-bis(Trimethylsilyl)-1,4-Phenylene bis(Trifluoromethanesulfonate)

Carpenter, C. A., Wegwerth, S. E. & Douglas, C. J., Sep 3 2019, In : Organic Preparations and Procedures International. 51, 5, p. 498-502 5 p.

Research output: Contribution to journalArticle

Rubrene Versus Fluorine-Functionalized Rubrene Molecules on a Metal Surface: Self-Assembly, Electronic Structure, and Energy Alignment of a Monolayer on Ag(100)

Viereck, J., Rangan, S., Häberle, P., Galoppini, E., Douglas, C. J. & Bartynski, R. A., Jun 13 2019, In : Journal of Physical Chemistry C. 123, 23, p. 14382-14390 9 p.

Research output: Contribution to journalArticle

3 Scopus citations

Synthesis of the Madangamine Alkaloid Core by a C-C Bond Activation Cascade

Eastwood, M. S. & Douglas, C. J., Aug 2 2019, In : Organic Letters. 21, 15, p. 6149-6154 6 p.

Research output: Contribution to journalArticle

3 Scopus citations
2018

Integrating Metal-Catalyzed C-H and C-O Functionalization to Achieve Sterically Controlled Regioselectivity in Arene Acylation

Serratore, N. A., Anderson, C. B., Frost, G. B., Hoang, T. G., Underwood, S., Gemmel, P., Hardy, M. A. & Douglas, C. J., Jun 19 2018, (Accepted/In press) In : Journal of the American Chemical Society.

Research output: Contribution to journalArticle

10 Scopus citations

Morphological, Chemical, and Electronic Changes of the Conjugated Polymer PTB7 with Thermal Annealing

Savikhin, V., Jagadamma, L. K., Purvis, L. J., Robertson, I., Oosterhout, S. D., Douglas, C. J., Samuel, I. D. W. & Toney, M. F., Apr 27 2018, In : iScience. 2, p. 182-192 11 p.

Research output: Contribution to journalArticle

Open Access
11 Scopus citations

Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations

Pan, Z., Wang, S., Brethorst, J. T. & Douglas, C. J., Mar 7 2018, In : Journal of the American Chemical Society. 140, 9, p. 3331-3338 8 p.

Research output: Contribution to journalArticle

18 Scopus citations

Synthesis and Characterization of Electron-Deficient Asymmetrically Substituted Diarylindenotetracenes

Purvis, L. J., Gu, X., Ghosh, S., Zhang, Z., Cramer, C. & Douglas, C. J., Feb 16 2018, In : Journal of Organic Chemistry. 83, 4, p. 1828-1841 14 p.

Research output: Contribution to journalArticle

4 Scopus citations
2017

Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions

Hoang, G. T., Walsh, D. J., McGarry, K. A., Anderson, C. B. & Douglas, C. J., Mar 17 2017, In : Journal of Organic Chemistry. 82, 6, p. 2972-2983 12 p.

Research output: Contribution to journalArticle

10 Scopus citations

Diastereoselective Intramolecular Cyanoamidation with Alkenes

Dreis, A. M., Otte, S. C., Eastwood, M. S., Alonzi, E. R., Brethorst, J. T. & Douglas, C. J., 2017, In : European Journal of Organic Chemistry. 2017, 1, p. 45-48 4 p.

Research output: Contribution to journalArticle

Open Access
6 Scopus citations
26 Scopus citations

Five fatty aldehyde dehydrogenase enzymes from Marinobacter and Acinetobacter spp. and structural insights into the aldehyde binding pocket

Bertram, J. H., Mulliner, K. M., Shi, K., Plunkett, M. H., Nixon, P., Serratore, N. A., Douglas, C. J., Aihara, H. & Barney, B. M., Jun 1 2017, In : Applied and environmental microbiology. 83, 12, e00018-17.

Research output: Contribution to journalArticle

Open Access
2 Scopus citations

Intrinsic non-radiative voltage losses in fullerene-based organic solar cells

Benduhn, J., Tvingstedt, K., Piersimoni, F., Ullbrich, S., Fan, Y., Tropiano, M., McGarry, K. A., Zeika, O., Riede, M. K., Douglas, C. J., Barlow, S., Marder, S. R., Neher, D., Spoltore, D. & Vandewal, K., Jan 1 2017, In : Nature Energy. 2, 6, 17053.

Research output: Contribution to journalArticle

192 Scopus citations

Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation

Frost, G. B., Serratore, N. A., Ogilvie, J. M. & Douglas, C. J., Apr 7 2017, In : Journal of Organic Chemistry. 82, 7, p. 3721-3726 6 p.

Research output: Contribution to journalArticle

Open Access
7 Scopus citations

Negative Isotope Effect on Field-Effect Hole Transport in Fully Substituted 13C-Rubrene

Ren, X., Bruzek, M. J., Hanifi, D. A., Schulzetenberg, A., Wu, Y., Kim, C. H., Zhang, Z., Johns, J. E., Salleo, A., Fratini, S., Troisi, A., Douglas, C. J. & Frisbie, C. D., Apr 1 2017, In : Advanced Electronic Materials. 3, 4, 1700018.

Research output: Contribution to journalArticle

11 Scopus citations

Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Ogden, W. A., Ghosh, S., Bruzek, M. J., Mcgarry, K. A., Balhorn, L., Young, V., Purvis, L. J., Wegwerth, S. E., Zhang, Z., Serratore, N. A., Cramer, C. J., Gagliardi, L. & Douglas, C. J., Feb 1 2017, In : Crystal Growth and Design. 17, 2, p. 643-658 16 p.

Research output: Contribution to journalArticle

10 Scopus citations

Scanning Kelvin Probe Microscopy Reveals Planar Defects Are Sources of Electronic Disorder in Organic Semiconductor Crystals

Wu, Y., Ren, X., Mcgarry, K. A., Bruzek, M. J., Douglas, C. J. & Frisbie, C. D., Jul 1 2017, In : Advanced Electronic Materials. 3, 7, 1700117.

Research output: Contribution to journalArticle

2 Scopus citations
2016

Synthesis, electrochemical properties, and crystal packing of perfluororubrene

Zhang, Z., Ogden, W. A., Young, V. G. & Douglas, C. J., Jan 1 2016, In : Chemical Communications. 52, 52, p. 8127-8130 4 p.

Research output: Contribution to journalArticle

7 Scopus citations
2015

Cyclization of an alkene-bearing cyclopentanone: The role of rhodium and Brønsted acid

Jiang, X., Pan, Z. & Douglas, C. J., Aug 22 2015, In : Tetrahedron Letters. 56, 39, p. 5324-5327 4 p.

Research output: Contribution to journalArticle

5 Scopus citations
2014

Carbon–Carbon Bond Activation with 8-Acylquinolines

Dreis, A. M. & Douglas, C. J., Jan 1 2014, In : Topics in Current Chemistry. 346, p. 85-110 26 p.

Research output: Contribution to journalArticle

9 Scopus citations

Intramolecular aminocyanation of alkenes by N-CN bond cleavage

Pan, Z., Pound, S. M., Rondla, N. R. & Douglas, C. J., May 12 2014, In : Angewandte Chemie - International Edition. 53, 20, p. 5170-5174 5 p.

Research output: Contribution to journalArticle

40 Scopus citations

Intramolecular oxyacylation of alkenes using a hydroxyl directing group

Hoang, G. T., Pan, Z., Brethorst, J. T. & Douglas, C. J., Dec 5 2014, In : Journal of Organic Chemistry. 79, 23, p. 11383-11394 12 p.

Research output: Contribution to journalArticle

9 Scopus citations

Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles

Rondla, N. R., Ogilvie, J. M., Pan, Z. & Douglas, C. J., Aug 18 2014, In : Chemical Communications. 50, 64, p. 8974-8977 4 p.

Research output: Contribution to journalArticle

16 Scopus citations
2013

Connecting molecular structure and exciton diffusion length in rubrene derivatives

Mullenbach, T. K., McGarry, K. A., Luhman, W. A., Douglas, C. J. & Holmes, R. J., Jul 19 2013, In : Advanced Materials. 25, 27, p. 3689-3693 5 p.

Research output: Contribution to journalArticle

50 Scopus citations

High-mobility transistors based on single crystals of isotopically substituted rubrene- d 28

Xie, W., McGarry, K. A., Liu, F., Wu, Y., Ruden, P. P., Douglas, C. J. & Frisbie, C. D., Jul 1 2013, In : Journal of Physical Chemistry C. 117, 22, p. 11522-11529 8 p.

Research output: Contribution to journalArticle

55 Scopus citations

Rubrene-based single-crystal organic semiconductors: Synthesis, electronic structure, and charge-transport properties

McGarry, K. A., Xie, W., Sutton, C., Risko, C., Wu, Y., Young, V. G., Brédas, J. L., Frisbie, C. D. & Douglas, C. J., Jun 11 2013, In : Chemistry of Materials. 25, 11, p. 2254-2263 10 p.

Research output: Contribution to journalArticle

100 Scopus citations

Utilizing carbon nanotube electrodes to improve charge injection and transport in bis(trifluoromethyl)-dimethyl-rubrene ambipolar single crystal transistors

Xie, W., Prabhumirashi, P. L., Nakayama, Y., McGarry, K. A., Geier, M. L., Uragami, Y., Mase, K., Douglas, C. J., Ishii, H., Hersam, M. C. & Frisbie, C. D., Nov 26 2013, In : ACS Nano. 7, 11, p. 10245-10256 12 p.

Research output: Contribution to journalArticle

36 Scopus citations
2012

Cooperative catalysis approach to intramolecular hydroacylation

Beletskiy, E. V., Chava, S. & Douglas, C. J., Jul 20 2012, In : Journal of Organic Chemistry. 77, 14, p. 5884-5893 10 p.

Research output: Contribution to journalArticle

43 Scopus citations

Diarylindenotetracenes via a selective cross-coupling/C-H functionalization: Electron donors for organic photovoltaic cells

Gu, X., Luhman, W. A., Yagodkin, E., Holmes, R. J. & Douglas, C. J., Mar 16 2012, In : Organic Letters. 14, 6, p. 1390-1393 4 p.

Research output: Contribution to journalArticle

25 Scopus citations
2011

Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation

Hoang, G. T., Reddy, V. J., Nguyen, H. H. K. & Douglas, C. J., Feb 18 2011, In : Angewandte Chemie - International Edition. 50, 8, p. 1882-1884 3 p.

Research output: Contribution to journalArticle

24 Scopus citations

Palladium-Catalyzed C-CN activation for intramolecular cyanoesterification of alkynes

Rondla, N. R., Levi, S. M., Ryss, J. M., Berg, R. A. V. & Douglas, C. J., Apr 15 2011, In : Organic Letters. 13, 8, p. 1940-1943 4 p.

Research output: Contribution to journalArticle

37 Scopus citations

Preparation of 6,11-dihydroxy-5,12-tetracenedione

Yagodkin, E., McGarry, K. A. & Douglas, C. J., Aug 10 2011, In : Organic Preparations and Procedures International. 43, 4, p. 360-363 4 p.

Research output: Contribution to journalArticle

4 Scopus citations
2010

Catalytic C-CN activation and asymmetric cyanoamidation of alkenes: Total syntheses of (+)-horsfiline, (-)-coerulescine, and (-)-esermethole

Reddy, V. J. & Douglas, C. J., Jun 26 2010, In : Tetrahedron. 66, 26, p. 4719-4729 11 p.

Research output: Contribution to journalArticle

19 Scopus citations

Highly enantioselective intramolecular cyanoamidation: (+)-horsfiline, (-)-coerulescine, and (-)-esermethole

Reddy, V. J. & Douglas, C. J., Mar 5 2010, In : Organic Letters. 12, 5, p. 952-955 4 p.

Research output: Contribution to journalArticle

48 Scopus citations

Low temperature Kumada-Corriu cross-coupling of polychlorinated acene derivatives and a synthesis of sterically demanding acenes

Yagodkin, E. & Douglas, C. J., Jun 9 2010, In : Tetrahedron Letters. 51, 23, p. 3037-3040 4 p.

Research output: Contribution to journalArticle

23 Scopus citations
2009

Catalytic carbon-carbon σ bond activation: An intramolecular carbo-acylation reaction with acylquinolines

Dreis, A. M. & Douglas, C. J., Jan 21 2009, In : Journal of the American Chemical Society. 131, 2, p. 412-413 2 p.

Research output: Contribution to journalArticle

153 Scopus citations

Chemoselectivity in catalytic C-C and C-H bond activation: Controlling intermolecular carboacylation and hydroarylation of alkenes

Wentzel, M. T., Reddy, V. J., Hyster, T. K. & Douglas, C. J., Oct 19 2009, In : Angewandte Chemie - International Edition. 48, 33, p. 6121-6123 3 p.

Research output: Contribution to journalArticle

94 Scopus citations

Synthesis, solid state properties, and semiconductor measurements of 5,6,11,12-tetrachlorotetracene

Yagodkin, E., Xia, Y., Kalihari, V., Frisbie, C. D. & Douglas, C. J., Sep 17 2009, In : Journal of Physical Chemistry C. 113, 37, p. 16544-16548 5 p.

Research output: Contribution to journalArticle

19 Scopus citations
2008

Increased efficiency in cross-metathesis reactions of sterically hindered olefins

Stewart, I. C., Douglas, C. J. & Grubbs, R. H., Feb 7 2008, In : Organic Letters. 10, 3, p. 441-444 4 p.

Research output: Contribution to journalArticle

130 Scopus citations
2007

Total synthesis of (-)-sarain A

Becker, M. H., Chua, P., Downham, R., Douglas, C. J., Garg, N. K., Hiebert, S., Jaroch, S., Matsuoka, R. T., Middleton, J. A., Ng, F. W. & Overman, L. E., Sep 12 2007, In : Journal of the American Chemical Society. 129, 39, p. 11987-12002 16 p.

Research output: Contribution to journalArticle

81 Scopus citations
2005

Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs

Anderson, C. E., Donde, Y., Douglas, C. J. & Overman, L. E., Jan 21 2005, In : Journal of Organic Chemistry. 70, 2, p. 648-657 10 p.

Research output: Contribution to journalArticle

118 Scopus citations
23 Scopus citations
2003

A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides

Frederick, M. O., Mulder, J. A., Tracey, M. R., Hsung, R. P., Huang, J., Kurtz, K. C. M., Shen, L. & Douglas, C. J., Mar 5 2003, In : Journal of the American Chemical Society. 125, 9, p. 2368-2369 2 p.

Research output: Contribution to journalArticle

200 Scopus citations

A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes

Shen, H. C., Wang, J., Cole, K. P., McLaughlin, M. J., Morgan, C. D., Douglas, C. J., Hsung, R. P., Coverdale, H. A., Gerasyuto, A. I., Hahn, J. M., Liu, J., Sklenicka, H. M., Wei, L. L., Zehnder, L. R. & Zificsak, C. A., Mar 7 2003, In : Journal of Organic Chemistry. 68, 5, p. 1729-1735 7 p.

Research output: Contribution to journalArticle

76 Scopus citations
2001

Efficient preparations of novel ynamides and allenamides

Wei, L. L., Mulder, J. A., Xiong, H., Zificsak, C. A., Douglas, C. J. & Hsung, R. P., Jan 14 2001, In : Tetrahedron. 57, 3, p. 459-466 8 p.

Research output: Contribution to journalArticle

123 Scopus citations
1999

Formal cycloaddition reactions of vinylogous amides with α,β-Unsaturated iminiums. A strategy for constructing piperidinyl heterocycles

Hsung, R. P., Wei, L. L., Sklenicka, H. M., Douglas, C. J., McLaughlin, M. J., Mulder, J. A. & Yao, L. J., Aug 12 1999, In : Organic Letters. 1, 3, p. 509-512 4 p.

Research output: Contribution to journalArticle

74 Scopus citations

Inverse demand [4+2] cycloaddition reactions of allenamides: Reactivity scopes of an electron deficient variant of allenamines

Wei, L. L., Xiong, H., Douglas, C. J. & Hsung, R. P., Sep 17 1999, In : Tetrahedron Letters. 40, 38, p. 6903-6907 5 p.

Research output: Contribution to journalArticle

59 Scopus citations
77 Scopus citations

Sequential 1,2-addition-electrocyclic ring closures involving acyclic α,β-unsaturated iminiums: A formal [3 + 3] cycloaddition strategy to unique pyranyl spirocycles

Hsung, R. P., Shen, H. C., Douglas, C. J., Morgan, C. D., Degen, S. J. & Yao, L. J., Feb 5 1999, In : Journal of Organic Chemistry. 64, 3, p. 690-691 2 p.

Research output: Contribution to journalArticle

89 Scopus citations