One-Pot Iridium Catalyzed C–H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes

Chotana, Ghayoor Abbas; Bastidas, Jose R. Montero; Miller, Susanne L.; Smith, Milton R.; Maleczka, Robert E.

doi:10.3390/molecules25071754

Cited by 5 publications

(6 citation statements)

References 56 publications

(125 reference statements)

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“…GC−MS (EI): m/z (%) = 307 (60) (M) + , 292 (41), 250 (100), 208 (71), 172 (30), 99 (20), 82 (75), 67 (28).…”

Section: Acsmentioning

confidence: 99%

“…GC−MS (EI): m/z (%) = 331 (8) (M) + , 316 (19), 288 (43), 287 (15), 273 (100), 272 (89), 271 (24), 256 (17), 246 (32), 245 (11), 232 (41), 231 (18), 230 (33), 229 (20), 200 (23), 191 (10), 190 (10).…”

Section: ■ Associated Contentmentioning

confidence: 99%

“…GC−MS (EI): m/z (%) = 359 (100) (M) + , 340 (35), 309 (59), 291 (23), 290 (96), 290 (96), 271 (15), 270 (52), 269 (49), 243 (30), 240 (11), 221 (26), 220 (68), 202 (14), 201 (27), 200 (20), 194 (11), 193 (12).…”

Section: ■ Associated Contentunclassified

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Iridium-Catalyzed C–H Borylation of CF₃-Substituted Pyridines

et al. 2022

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Iridium-catalyzed C–H borylation of CF 3 -substituted pyridines is described in this paper. The boronic ester group can be installed on the α, β, or γ position of pyridine by an appropriate substitution pattern. Sterically governed regioselectivity provides convenient access to a variety of CF 3 -substituted pyridylboronic esters. These catalytic C–H borylation reactions were carried out neatly without the use of any solvent. Several functional groups, such as halo, ester, alkoxy, amino, etc., are compatible with this methodology. These pyridylboronic esters are amenable to column chromatography and the products were isolated in good to excellent yields. α-Borylated pyridines, although isolated in good yields, do not have a long shelf life. The boronic ester derivatives of these CF 3 -substituted pyridines can serve as useful precursors in the synthesis regime.

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“…GC−MS (EI): m/z (%) = 307 (60) (M) + , 292 (41), 250 (100), 208 (71), 172 (30), 99 (20), 82 (75), 67 (28).…”

Section: Acsmentioning

confidence: 99%

Section: ■ Associated Contentmentioning

confidence: 99%

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Iridium-Catalyzed C–H Borylation of CF₃-Substituted Pyridines

et al. 2022

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“…On the other side, N−H unprotected pyrroleboronic esters have been much less utilized for Suzuki coupling [ 78 ]. Our group has been interested in exploring catalytic C–H borylation reactions for organic synthesis [ 72 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 ]. A recent report about failure of installation of highly electron-rich aromatic substituent on pyrrole by direct arylation [ 52 ] prompted us to investigate Suzuki coupling route for this purpose.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling

et al. 2020

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A convenient two-step preparation of NH-free 5-aryl-pyrrole-2-carboxylates is described. The synthetic route consists of catalytic borylation of commercially available pyrrole-2-carboxylate ester followed by Suzuki coupling without going through pyrrole N–H protection and deprotection steps. The resulting 5-aryl substituted pyrrole-2-carboxylates were synthesized in good- to excellent yields. This synthetic route can tolerate a variety of functional groups including those with acidic protons on the aryl bromide coupling partner. This methodology is also applicable for cross-coupling with heteroaryl bromides to yield pyrrole-thiophene, pyrrole-pyridine, and 2,3’-bi-pyrrole based bi-heteroaryls.

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“…The high chemoselectivity exhibited by transition-metal-catalyzed cross-coupling reactions can be exploited to develop various synthetic transformations using one-pot procedures. In this issue, Malezcka, Smith et al describe the efficient combination of the regioselective iridium-catalyzed C–H borylation of aryl halides with the Sonogashira coupling [ 29 ]. Interestingly, the coupling reaction takes place selectively at the carbon–halogen bond allowing the preparation of novel alkynyl boron reagents.…”

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confidence: 99%