Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-chloromethyl-2,1-borazaronaphthalene

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2014 Oct 16

PMID 25317850

Citations 12

Authors

Gary A Molander

Steven R Wisniewski

Javad Amani

Affiliations

Soon will be listed here.

Abstract

One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This B-N isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.

Citing Articles

The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Liu Y, Puig de la Bellacasa R, Li B, Cuenca A, Liu S J Am Chem Soc. 2021; 143(35):14059-14064.

PMID: 34431676 PMC: 9165608. DOI: 10.1021/jacs.1c06112.

Selectivity in the Elaboration of Bicyclic Borazarenes.

Bhattacharjee A, Davies G, Saeednia B, Wisniewski S, Molander G Adv Synth Catal. 2021; 363(9):2256-2273.

PMID: 34335130 PMC: 8323665. DOI: 10.1002/adsc.202001384.

One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids.

Ouadoudi O, Kaehler T, Bolte M, Lerner H, Wagner M Chem Sci. 2021; 12(16):5898-5909.

PMID: 34168815 PMC: 8179653. DOI: 10.1039/d1sc00543j.

Expanding the functional group tolerance of cross-coupling in 1,2-dihydro-1,2-azaborines: installation of alkyl, alkenyl, aryl, and heteroaryl substituents while maintaining a B-H bond.

Brown A, Li B, Liu S Tetrahedron. 2019; 75(5):580-583.

PMID: 31537948 PMC: 6752210. DOI: 10.1016/j.tet.2018.12.039.

Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins.

Boknevitz K, Italia J, Li B, Chatterjee A, Liu S Chem Sci. 2019; 10(19):4994-4998.

PMID: 31183048 PMC: 6524624. DOI: 10.1039/c8sc05167d.

References

Liu Z, Marder T . B-N versus C-C: how similar are they?. Angew Chem Int Ed Engl. 2007; 47(2):242-4. DOI: 10.1002/anie.200703535. View

Sun N, Fu J, Weng J, Jin J, Tan C, Liu X . Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel 1,2,4-triazole derivatives containing the 1,2,3-thiadiazole moiety. Molecules. 2013; 18(10):12725-39. PMC: 6270153. DOI: 10.3390/molecules181012725. View

Grassberger M, Turnowsky F, Hildebrandt J . Preparation and antibacterial activities of new 1,2,3-diazaborine derivatives and analogues. J Med Chem. 1984; 27(8):947-53. DOI: 10.1021/jm00374a003. View

Roche O, Sarmiento R . A new class of histamine H3 receptor antagonists derived from ligand based design. Bioorg Med Chem Lett. 2007; 17(13):3670-5. DOI: 10.1016/j.bmcl.2007.04.056. View

Wisniewski S, Guenther C, Argintaru O, Molander G . A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates. J Org Chem. 2013; 79(1):365-78. PMC: 3932559. DOI: 10.1021/jo402616w. View

Campbell P, Marwitz A, Liu S . Recent advances in azaborine chemistry. Angew Chem Int Ed Engl. 2012; 51(25):6074-92. PMC: 3698317. DOI: 10.1002/anie.201200063. View

Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

Pan J, Kampf J, Ashe 3rd A . Electrophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborines. Org Lett. 2007; 9(4):679-81. DOI: 10.1021/ol062968r. View

Becer C, Hoogenboom R, Schubert U . Click chemistry beyond metal-catalyzed cycloaddition. Angew Chem Int Ed Engl. 2009; 48(27):4900-8. DOI: 10.1002/anie.200900755. View

10.

Levy C, Baldock C, Wallace A, Sedelnikova S, Viner R, Clough J . A study of the structure-activity relationship for diazaborine inhibition of Escherichia coli enoyl-ACP reductase. J Mol Biol. 2001; 309(1):171-80. DOI: 10.1006/jmbi.2001.4643. View

11.

Ashton W, Canning L, Reynolds G, Tolman R, KARKAS J, Liou R . Synthesis and antiherpetic activity of (S)-, (R)-, and (+/-)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine. J Med Chem. 1985; 28(7):926-33. DOI: 10.1021/jm00145a014. View

12.

Knack D, Marshall J, Harlow G, Dudzik A, Szaleniec M, Liu S . BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues. Angew Chem Int Ed Engl. 2013; 52(9):2599-601. PMC: 3748812. DOI: 10.1002/anie.201208351. View

13.

Baldock C, de Boer G, Rafferty J, Stuitje A, Rice D . Mechanism of action of diazaborines. Biochem Pharmacol. 1998; 55(10):1541-9. DOI: 10.1016/s0006-2952(97)00684-9. View