168265-56-3Relevant articles and documents
Pd(ii)-catalyzed, controllable C-H mono-/diarylation of aryl tetrazoles: Concise synthesis of Losartan
Ding, Yan-Jun,Li, Yan,Dai, Sheng-Yu,Lan, Quan,Wang, Xi-Sheng
, p. 3198 - 3201 (2015)
A palladium(ii)-catalyzed C-H arylation directed by tetrazole, a metabolically stable surrogate for the carboxylic acid group in drug design, has been developed. Excellent mono-/di-selectivity was achieved through adjustment of the protecting site on the tetrazole ring. The synthetic utility of this new transformation was demonstrated in the concise total synthesis of Losartan. This journal is
Cobalt-catalyzed C-H arylations with weakly-coordinating amides and tetrazoles: Expedient route to angiotensin-ii-receptor blockers
Li, Jie,Ackermann, Lutz
supporting information, p. 5718 - 5722 (2015/03/31)
Cobalt-catalyzed C-H arylations enabled the synthesis of biaryl tetrazoles, which are key structural motifs in antihypertensive angiotensin-II-receptor blockers. Thus, weakly-coordinating benzamides were employed for step-economical C-H arylations with ample scope. Further, a low-valent NHC complex enabled first cobalt-catalyzed C-H functionalization by tetrazole assistance.
Carboxylate-assisted ruthenium(II)-catalyzed C-H arylations of 5-aryl tetrazoles: Step-economical access to Valsartan
Diers, Emelyne,Phani Kumar,Mejuch, Tom,Marek, Ilan,Ackermann, Lutz
, p. 4445 - 4453 (2013/06/27)
Carboxylate assistance was key to success for highly efficient ruthenium-catalyzed direct ortho-arylations of tetrazolyl-substituted arenes with aryl halides and triflates in the absence of phosphine ligands. Thus, ruthenium(II) biscarboxylates allowed for C-H bond functionalizations with excellent chemo- and site-selectivities, which set the stage for an atom- and step-economical access to key angiotensin-II-receptor blockers. Mechanistic studies revealed the C-H bond metalation to be reversible, and were suggestive of a rate-determining reductive elimination.