2002
DOI: 10.1021/jo010707j
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Preparation of 5-Brominated and 5,5‘-Dibrominated 2,2‘-Bipyridines and 2,2‘-Bipyrimidines

Abstract: Efficient syntheses of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines, useful for the preparation of metal-complexing molecular rods, have been developed. 5-Bromo-2,2'-bipyridine, 5-bromo-5'-n-butyl-2,2'-bipyridine, and 5-bromo-5'-n-hexyl-2,2'-bipyridine were obtained by Stille coupling of 2,5-dibromopyridine with 2-trimethylstannylpyridine or the requisite 5-alkyl-2-trimethylstannylpyridine, obtained via regioselective zincation of a 3-alkylpyridine.BF(3) complex in the less hinder… Show more

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Cited by 166 publications
(117 citation statements)
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“…The essential step for the synthesis of ligands L5 and L6 was the Stille coupling [38] of 2-trimethylstannylpyridine (11) [39] or 2-trimethyl-stannyl-5-octylthiophene (14) with the brominated terpyridine carbonitriles 8 and 9, respectively, as shown in Scheme 2. 2-Trimethylstannylpyridine was obtained by lithiation followed by transmetalation with trimethyltin chloride of 2-bromopyridine (10), whereas 2-trimethylstannyl-5-octylthiophene was obtained by the same method starting directly from 2-octylthiophene.…”
Section: Resultsmentioning
confidence: 99%
“…The essential step for the synthesis of ligands L5 and L6 was the Stille coupling [38] of 2-trimethylstannylpyridine (11) [39] or 2-trimethyl-stannyl-5-octylthiophene (14) with the brominated terpyridine carbonitriles 8 and 9, respectively, as shown in Scheme 2. 2-Trimethylstannylpyridine was obtained by lithiation followed by transmetalation with trimethyltin chloride of 2-bromopyridine (10), whereas 2-trimethylstannyl-5-octylthiophene was obtained by the same method starting directly from 2-octylthiophene.…”
Section: Resultsmentioning
confidence: 99%
“…[34] 1,3-dibromo-5-diphenylphosphino benzene (13), [35] [(h 5 -C 5 Me 5 )RhCl 2 ] 2 (18), [36] [(Et 2 S) 2 PtCl 2 ] (20), [37] [(tht)AuCl] (22), [38] 5-ethynyl-2,2'-bipyridyl (23), [39] [(nbd)Mo(CO) 4 ] (27) [40] [41] were prepared according to published procedures. All other chemicals were purchased from commercial suppliers and were used as received.…”
Section: -Dppf)a C H T U N G T R E N N U N G (H 5 -C 5 H 5 )Rucl] (7)mentioning
confidence: 99%
“…[6] Our syntheses of the C-nucleosides 1 a and 1 b followed established routes in C-glycoside chemistry [27,28] (Scheme 1) and started with 2,3,5-tri-O-benzyl-d-ribonolactone 2 [29] as the common deoxyribose precursor to which the lithiated 4-bromo-2,2-biphenyl 3 a or 5-iodo-2,2-bipyridine 3 b [30,31] were added. While 3 a is commercially available, 3 b had to be prepared in three steps by stannylation of 2-bromopyridine 4 (!5), [32] followed by a [Pd(PPh 3 ) 4 ] catalyzed Stille coupling with 2,5-dibromopyridine and a subsequent copper(i)-catalyzed halogen-exchange reaction (Scheme 2). The halogen exchange was necessary as, in our hands, the intermediate 5-bromo-2,2-bipyridine 6 [32] failed to react to the coupled product 7 b by the standard procedure.…”
Section: Synthesis Of Monomersmentioning
confidence: 99%