Gary A. Molander

University of Pennsylvania

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Christopher B. Kelly

Johnson & Johnson (United States)

Deidre L. Sandrock

Philadelphia University

Shorouk O. Badir

University of Pennsylvania

Christina R. Harris

Temple College

Jennifer K. Matsui

The Ohio State University

Steven R. Wisniewski

Bristol-Myers Squibb (United States)

Albert Granados

Universitat Autònoma de Barcelona

ÁG

Álvaro Gutiérrez‐Bonet

United States Military Academy

Belgin Canturk

Corteva (United States)

Lívia N. Cavalcanti

Universidade Federal do Rio Grande do Norte

Cooperative Institutions

University of Pennsylvania

184

Philadelphia University

128

Robert Bosch (Germany)

101

Centre National de la Recherche Scientifique

University of Colorado Boulder

California University of Pennsylvania

Merck & Co., Inc., Rahway, NJ, USA (United States)

ETH Zurich

Harvard University

Massachusetts Institute of Technology

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Sequential Ketyl−Olefin Coupling/β-Elimination Reactions Mediated by Samarium(II) Iodide

The Journal of Organic Chemistry (1998)

Gary A. Molander Christina R. Harris

Samarium(II) iodide (SmI(2)) has been employed in an intramolecular sequential ketyl-olefin coupling/beta-elimination reaction. The overall process results in the net addition of an alkenyl species to a ketone carbonyl. This novel protocol for the intramolecular delivery of an alkenyl moiety avoids the basic reaction conditions typical of nucleophilic additions that are mediated by alkenylmagnesium halides and alkenyllithium reagents. A high degree of stereocontrol is imparted in the SmI(2)-mediated process as a result of the excellent facial selectivity conveyed in the initial ketyl-olefin coupling reaction. The relative asymmetric induction engendered in these addition reactions is complementary to more traditional nucleophilic addition reactions in that the alkenyl group is directed to the carbonyl center by an attached tether.

Ketyl

Moiety

Coupling reaction

Intramolecular reaction

Nucleophilic Addition

10.1021/jo971889d

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Citations (25)

Stereocontrolled [m + n] annulation reactions. 2. A [3 + 3] route to chiral, nonracemic 1,2-cyclohexanediols

Journal of the American Chemical Society (1987)

Gary A. Molander David C. Shubert

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStereocontrolled [m + n] annulation reactions. 2. A [3 + 3] route to chiral, nonracemic 1,2-cyclohexanediolsGary A. Molander and David C. ShubertCite this: J. Am. Chem. Soc. 1987, 109, 2, 576–578Publication Date (Print):January 1, 1987Publication History Published online1 May 2002Published inissue 1 January 1987https://pubs.acs.org/doi/10.1021/ja00236a042https://doi.org/10.1021/ja00236a042research-articleACS PublicationsRequest reuse permissionsArticle Views348Altmetric-Citations49LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Annulation

10.1021/ja00236a042

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Citations (52)

Conjugate Addition Reactions Mediated by Samarium(II) Iodide

The Journal of Organic Chemistry (1997)

Gary A. Molander Christina R. Harris

Samarium(II) iodide in conjunction with a catalytic low-valent transition metal species has been employed to promote the conjugate addition reaction of primary and secondary alkyl halides onto α,β-unsaturated esters and amides. The method has been determined to be quite general and hence has been extended to the cyclization reactions of alkyl halides onto α,β-unsaturated lactones, lactams, and nitriles. The cyclization reactions described herein provide a very general approach to the synthesis of functionalized carbocycles from simple acyclic precursors with excellent diastereoselectivity and under very mild reaction conditions.

Conjugate

10.1021/jo971047e

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Citations (74)

Palladium-catalyzed cross-coupling reaction of alkenyl bromides with potassium alkyltrifluoroborates

Tetrahedron (2006)

Gary A. Molander Jungyeob Ham Dave G. Seapy

Coupling reaction

10.1016/j.tet.2006.10.088

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Citations (36)

Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations

Chem (2020)

Shorouk O. Badir Gary A. Molander

Photoredox catalysis

Catalytic cycle

Heteroatom

10.1016/j.chempr.2020.05.013

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Citations (231)

A facile synthesis of 2‐aminothiazolo[5,4‐b]‐ and 2‐aminothiazolo[4,5‐c] pyridines

Journal of Heterocyclic Chemistry (1977)

Henry W. Aitland Gary A. Molander

Abstract The hydrochlorides of the title compounds are obtained in moderate yields by refluxing 2‐chloro‐3‐aminopyridine or 3‐amino‐4‐chloropyridine, respectively, with an alkyl. Aralkyl‐, or aryl isothiocyanate in absolute ethanol solution. A proof is presented that the 2‐aminothiazolopyridine hydrochloride and not the isomeric o ‐chloropyridylthiourea is the product of this reaction. The free‐bases may be obtained from the hydrochlorides with aqueous sodium bicarbonate. A mechanism for the formation of the thiazole ring is briefly considered. The interactions of 2‐chloro‐3‐aminopyridine with l‐substituted‐5‐mereapto‐1 H ‐tetrazoles are also described.

Thiazole

Hydrochloride

Sodium bicarbonate

Phenyl isothiocyanate

10.1002/jhet.5570140125

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Citations (24)

Lanthanides in organic synthesis. 2. Reduction of .alpha.-heterosubstituted ketones

The Journal of Organic Chemistry (1986)

Gary A. Molander Gregory Hahn

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLanthanides in organic synthesis. 2. Reduction of .alpha.-heterosubstituted ketonesGary A. Molander and Gregory HahnCite this: J. Org. Chem. 1986, 51, 7, 1135–1138Publication Date (Print):April 1, 1986Publication History Published online1 May 2002Published inissue 1 April 1986https://pubs.acs.org/doi/10.1021/jo00357a040https://doi.org/10.1021/jo00357a040research-articleACS PublicationsRequest reuse permissionsArticle Views4869Altmetric-Citations278LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Alpha (finance)

10.1021/jo00357a040

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Citations (289)

C-1 Building Blocks in Organic Synthesis 2

Piet W. N. M. van Leeuwen Roberto Ballini Tomás R. Belderraín C. Bruneau Mirza Cokoja

10.1055/b-003-125817

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Citations (8)

ChemInform Abstract: Regiochemical Control in the Intramolecular Addition of Allylstannanes and Allylsilanes to 2,3‐Epoxy Ethers: Preparation of Functionalized Oxepanes.

ChemInform (1989)

Gary A. Molander Steven W. Andrews

Abstract The hydroxymethyloxiranes (I) are coupled with the silyl‐ or stannylpropenyl methanesulfonates (II) to yield the metallated methallyl ethers (III).

10.1002/chin.198948212

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Sustainable Thioetherification via Electron Donor–Acceptor Photoactivation Using Thianthrenium Salts

Angewandte Chemie International Edition (2022)

María Jesús Cabrera‐Afonso Albert Granados Gary A. Molander

Abstract The synthesis of sulfides has been widely studied because this functional subunit is prevalent in biomolecules and pharmaceuticals, as well as being a useful synthetic platform for further elaboration. Thus, various methods to build C−S bonds have been developed, but typically they require the use of precious metals or harsh conditions. Electron donor–acceptor (EDA) complex photoactivation strategies have emerged as versatile and sustainable ways to achieve C−S bond formation, avoiding challenges associated with previous methods. This work describes an open‐to‐air, photoinduced, site‐selective C−H thioetherification from readily available reagents via EDA complex formation that tolerates a wide range of different functional groups. Moreover, C(sp 2 )−halogen bonds remain intact using this protocol, allowing late‐stage installation of the sulfide motif in various bioactive scaffolds, while allowing yet further modification through more traditional C−X bond cleavage protocols. Additionally, various mechanistic investigations support the envisioned EDA complex scenario.

Electron acceptor

Electron donor

Biomolecule

Acceptor

Structural motif

10.1002/anie.202202706

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Citations (132)