References
- (a) Miyaura N, Suzuki A. Stereoselective synthesis of arylated (E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst. J Chem Soc, Chem Commun 1979;19:866-867.
- (b) Miyaura N, Suzuki A. Palladium-catalyzed crosscoupling reactions of organoboron compounds. Chem Rev 1995;95:2457-2483. https://doi.org/10.1021/cr00039a007
- (c) Suzuki A. Organoborates in new synthetic reactions. Acc Chem Res 1982;15:178-184. https://doi.org/10.1021/ar00078a003
- (a) Brown HC, Cole TE. Organoboranes. 31. A simple preparation of boronic esters from organolithium reagents and selected trialkoxyboranes. Organometallics 1983;2:1316-1319. https://doi.org/10.1021/om50004a009
- (b) Lappert MF. Organic compounds of boron. Chem Rev 1956;56:959-1064. https://doi.org/10.1021/cr50011a002
- (c) Letsinger RL, Skoog IH. The preparation and some properties of 2-methyl-1-propene-1-boronic acid. J Org Chem 1953;18:895-897. https://doi.org/10.1021/jo50013a019
-
(d) Yamamura M, Moritani I, Murahashi SI. The reaction of
${\sigma}-vinylpalladium$ complexes with alkyllithiums. Stereospecific syntheses of olefins from vinyl halides and alkyllithiums. J Organomet Chem 1975;91:C39-C42. https://doi.org/10.1016/S0022-328X(00)89636-9 - Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF. C−H activation for the construction of C−B bonds. Chem Rev 2010;110:890-931. https://doi.org/10.1021/cr900206p
- (a) Cho JY, Tse MK, Holmes D, Maleczka RE, Smith MR. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds. Science 2002;295:305-308. https://doi.org/10.1126/science.1067074
- (b) Larsen MA, Hartwig JF. Iridium-catalyzed C-H borylation of heteroarenes: scope, regioselectivity, application to late-stage functionalization, and mechanism. J Am Chem Soc 2014;136:4287-4299. https://doi.org/10.1021/ja412563e
- Cho JY, Iverson CN, Smith MR. Steric and chelate directing effects in aromatic borylation. J Am Chem Soc 2000;122:12868-12869. https://doi.org/10.1021/ja0013069
- (a) Labinger JA. Platinum-catalyzed C-H functionalization. Chem Rev 2017;117:8483-8496. https://doi.org/10.1021/acs.chemrev.6b00583
- (b) Furukawa T, Tobisu M, Chatani N. C-H borylation by platinum catalysis. Bull Chem Soc Jpn 2017;90:332-342. https://doi.org/10.1246/bcsj.20160391
- (a) Norio M. Metal-catalyzed reactions of organoboronic acids and esters. Bull Chem Soc Jpn 2008;81:1535-1553. https://doi.org/10.1246/bcsj.81.1535
- (b) Primas N, Bouillon A, Rault S. Recent progress in the synthesis of five-membered heterocycle boronic acids and esters. Tetrahedron 2010;66:8121-8136. https://doi.org/10.1016/j.tet.2010.08.001
- (c) Pilarski LT, Szabo KJ. Palladium-catalyzed direct synthesis of organoboronic acids. Angew Chem Int Ed 2011;50:8230-8232. https://doi.org/10.1002/anie.201102384
- (a) Ohe T, Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates. J Org Chem 1993;58:2201-2208. https://doi.org/10.1021/jo00060a041
- (b) Percec V, Bae JY, Hill DH. Aryl mesylates in metal catalyzed homocoupling and cross-coupling reactions. 2. Suzuki-type nickel-catalyzed cross-coupling of aryl arenesulfonates and aryl mesylates with arylboronic acids. J Org Chem 1995;60:1060-1065. https://doi.org/10.1021/jo00109a044
-
(a) Takise R, Muto K, Yamaguchi J, Itami K. Nickelcatalyzed
${\alpha}-arylation$ of ketones with phenol derivatives. Angew Chem Int Ed 2014;53:6791-6794. https://doi.org/10.1002/anie.201403823 - (b) Muto K, Yamaguchi J, Itami K. Nickel-catalyzed C-H/C-O coupling of azoles with phenol derivatives. J Am Chem Soc 2012;134:169-172. https://doi.org/10.1021/ja210249h
- Mahatthananchai J, Dumas AM, Bode JW. Catalytic selective synthesis. Angew Chem Int Ed 2012;51:10954-10990. https://doi.org/10.1002/anie.201201787
- (a) Sibi MP, Snieckus V. The directed ortho lithiation of O-aryl carbamates. An anionic equivalent of the Fries rearrangement. J Org Chem 1983;48:1935-1937. https://doi.org/10.1021/jo00159a040
- (b) Waltz KM, Muhoro CN, Hartwig JF. C−H activation and functionalization of unsaturated hydrocarbons by transition-metal boryl complexes. Organometallics 1999;18:3383-3393. https://doi.org/10.1021/om990113v
- (c) Pena MA, Perez Sestelo J, Sarandeses LA. Palladium-catalyzed aryl−aryl crosscoupling reaction using ortho-substituted arylindium reagents. J Org Chem 2007;72:1271-1275. https://doi.org/10.1021/jo062148s
- (d) Cornella J, Zarate C, Martin R. Metal-catalyzed activation of ethers via C−O bond cleavage: a new strategy formolecular diversity. Chem Soc Rev 2014;43:8081-8097. https://doi.org/10.1039/C4CS00206G
- (e) Xue C, Luo Y, Teng H, Ma Y, Nishiura M, Hou Z. Ortho-selective C-H borylation of aromatic ethers with pinacol-borane by organo rare-earth catalysts. ACS Catal 2018:5017-5022.
- Wilson DA, Wilson CJ, Moldoveanu C, Resmerita AM, Corcoran P, Hoang LM, Rosen BM, Percec V. Neopentylglycolborylation of aryl mesylates and tosylates catalyzed by Ni-based mixed-ligand systems activated with Zn. J Am Chem Soc 2010;132:1800-1801. https://doi.org/10.1021/ja910808x
- (a) Wenkert E, Michelotti EL, Swindell CS. Nickelinduced conversion of carbon-oxygen into carboncarbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls. J Am Chem Soc 1979;101:2246-2247. https://doi.org/10.1021/ja00502a074
- (b) Alvarez-Bercedo P, Martin R. Ni-catalyzed reduction of inert C−O bonds: A new strategy for using aryl ethers as easily removable directing groups. J Am Chem Soc 2010;132:17352-17353. https://doi.org/10.1021/ja106943q
- (c) Li BJ, Yu DG, Sun CL, Shi ZJ. Activation of "inert" alkenyl/aryl C-O bond and its application in cross-coupling reactions. Chemistry 2011;17:1728-1759. https://doi.org/10.1002/chem.201002273
- (d) Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita AM, Garg NK, Percec V. Nickelcatalyzed cross-couplings involving carbon-oxygen bonds. Chem Rev 2011;111:1346-1416. https://doi.org/10.1021/cr100259t
- (e) Tobisu M, Chatani N. Cross-couplings using aryl ethers via C-O bond activation enabled by nickel catalysts. Acc Chem Res 2015;48:1717-1726. https://doi.org/10.1021/acs.accounts.5b00051
- Zarate C, Manzano R, Martin R. Ipso-borylation of aryl ethers via Ni-catalyzed C–OMe cleavage. J AmChem Soc 2015;137:6754-6757. https://doi.org/10.1021/jacs.5b03955