Recent Advances in the Chemistry of the Organotin Hydrides

Abstract

Advances in the chemistry of the organotin hydrides during the last decade are reviewed.

Molecular Main Group Metal Hydrides

“…Tin hydrides are well known as sources of radicals for cyclization reactions in organic chemistry and for their use in the hydrometallation of unsaturated substrates. − As before, we will not describe every reaction involving a tin hydride since 2001, as there is frankly not enough time to cover such a vast field. In keeping with the theme of this review, we will document in this section developments pertaining to Sn­(II) hydrides and show how the interesting chemistry uncovered has promoted many new opportunities in tin-mediated catalysis.…”

“…1250 This bond length is significantly longer than that determined by single crystal X-ray crystallography 1159), presumably with the concomitant formation of metallic antimony. 1250 Similar to the bulky alkyl-substituted stibine {(Me 3 Si) 2 CH}-SbH 2 (1157), primary aryl-substituted stibines MesSbH 2 (1164) and Ar Me6 SbH 2 (1165) were synthesized from their respective chloride derivatives and Li[AlH 4 ] as a hydride source (Scheme 166). 1251,1252 Tilley and coworkers investigated the dehydrocoupling of 1164 and 1165 using the d 0 transition metal catalysts Cp 2 Zr(H)Cl and Cp*CpHf(H)-Cl.…”

“…1254 Another rare complex containing antimony hydrides in the coordination sphere of a metal was reported by Tilley and coworkers, using the dihydride bridged platinium dication salt [(dippe) 2 Pt(μ-H) 2 Pt(dippe) 2 ]{BAr F 4 } 2 as a precursor. When this diplatinum dihydride was combined with MesSbH 2 (1164) or Ar Me6 SbH 2 (1165) dihydrogen elimination was observed to give the primary antimonide-bridged platinum dications 1248 and 1249 (eq 106). 1288 In 2019, Driess and coworkers demonstrated a direct route to [Li(TMEDA)]-Scheme 177.…”

Synthetic utility of tribenzyltin hydride and its derivatives as easily accessible, removable, and decomposable organotin reagents

“…Unfortunately, synthetic use of Bu 3 SnH and their derivatives has two serious problems. Since the organotin byproducts Bu 3 SnX (X ¼ halogen, OH, OSnBu 3 ) have high lipophilicity, their removal by silica-gel column chromatography is difficult without pretreatment of the reaction mixture [1,8]. In addition, Bu 3 SnX are stable, hardly decomposable, and toxic [9].…”

Carbon, silicon, germanium, tin and lead

“…The exciting area of sila-and germa-cyclopropabenzenes has been reviewed by one of the outstanding contributors to the field. 11 Organotin chemistry has been a focus this year, with reviews on stannides and intermetallic tin compounds 12 advances in the chemistry of the organotin hydrides, 13 quantitative-structure activity relationships 14 the biological activity of cationic organotin(IV) complexes 15 and a very readable comparison of silyl and stannyl derivatives of ruthenium and osmium. 16 An entire issue of the Journal of Organometallic Chemistry devoted to organotin chemistry showcased a range of new developments.…”