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Reactions of the solution stable, two-coordinate hydrido-tetrylenes, :E(H)(L † ) (E = Ge or Sn; L † = -N(Ar † )(SiPr i  3 ); Ar † = C 6 H 2 {C(H)Ph 2 } 2 Pr i -2,6,4), with a variety of unactivated cyclic and acyclic alkenes, and one internal alkyne, lead to the rapid and regiospecific hydrometallation of the unsaturated substrate at ambient temperature. The products of the reactions, [L † E(C 2 H 4 R)] (E = Ge or Sn, R = H, Ph or Bu  t  ), [L † E{CH(CH 2 ) 3 (CH 2 )  n  }] (E = Ge, n = 1, 2 or 3; E = Sn, n = 1) and [L † E{C(Ph)[double bond, length as m-dash]C(H)(Me)}], include the first structurally characterised examples of two-coordinate amido/alkyl germylenes and stannylenes. The cycloalkene hydrometallation reactions are cleanly reversible under ambient conditions, a process which computational and experimental van't Hoff analyses suggest proceeds via β-hydride elimination from the metal coordinated cycloalkyl ligand. Similarly, the reactions of :Ge(H)(L † ) with 1,5-cyclooctadiene and 2-methyl-2-butene, both likely proceed via β-hydride elimination processes, leading to the clean isomerisation of the alkene involved, and its subsequent hydrogermylation, to give [L † Ge(2-cyclooctenyl)] and [L † Ge{C 2 H 4 C(H)Me 2 }], respectively. Reactions of [L † GeEt] and [L † Ge(C 5 H 9 )] with the protic reagents, HCl, NH 3 and EtOH, lead to oxidative addition to the germanium(ii) centre, and formation of the stable chiral germanium(iv) complexes, [L † Ge(C 5 H 9 )(H)Cl] and [L † Ge(Et)(H)R] (R = NH 2 or OEt). In contrast, related reactions between [L † SnEt] and Bu  t  OH or TEMPOH (TEMP = 2,2,6,6-tetramethylpiperidinyl) proceed via ethane elimination, affording the tin(ii) products, [L † SnR] (R = OBu  t  or OTEMP). In addition, the oxidation of [L † Ge(C 6 H 11 )] and [L † Sn(C 2 H 4 Bu  t  )] with O 2 yields the oxo-bridged metal(iv) dimers, [{L † (C 6 H 11 )Ge(μ-O)} 2 ] and [{L † (Bu  t  C 2 H 4 )Sn(μ-O)} 2 ], respectively.

chemical science

Two-coordinate group 14 element(<scp>ii</scp>) hydrides as reagents for the facile, and sometimes reversible, hydrogermylation/hydrostannylation of unactivated alkenes and alkynes

Two-coordinate group 14 element(ii) hydrides as reagents for the facile, and sometimes reversible, hydrogermylation/hydrostannylation of unactivated alkenes and alkynes