By A. Togni, H. Grützmacher
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There are no large differences in the yields and the reaction rates between internal and terminal alkynes and the reaction is available with various functional groups. The carbon-carbon double bond, chloro, epoxy, ester, cyano, and ketone carbonyl groups remain intact during the addition to the C-C triple bonds . The first synthesis of tetraborylethylene (catB)2C=C(Bcat)2 is MeO O OMe MeO O OMe 81 Me N PhMe2Si B N Me Ph Ph Ph Ph O PhMe2Ge B O O 88 Borylation Reagents O Ph O O Ph 86 O B O B B 85 PhMe2Si O 83 (catBBcat) O O B B O O Ph 87 O O Ph 84 O B B 82 (pinBBpin) O O B B O O Scheme 1-23 O O B B B B 89 Me N Me3Sn B N Me 90 23 24 1 Hydroboration, Diboration, Silylboration and Stannylboration R Pt(0) or Pd(0) catalyst + X B R H H X B 91 Entry X-B< R Catalyst 1 2 3 4 5 6 7 8 9 10 11 (MeO)2BB(OMe)2 catBBcat (83) pinBBpin (82) n-C6H13 n-C6H13 n-C6H13 Ph N≡C(CH2)3 MeO2C(CH2)4 n-C6H13 n-C6H13 n-C6H13 n-C6H13 Ph Pt(PPh3)4/80°C Pt(PPh3)4/80°C Pt(PPh3)4/80°C Pt(PPh3)4/80°C Pt(PPh3)4/80°C Pt(PPh3)4/80°C Pt(PPh3)4/120°C Pd2(dba)3/4etpo/80°Ca) Pd(OAc)2/15RNC/110°Cb) Pd(PPh3)4/rt Pd(PPh3)4/rt (Me2N)2BB(NMe2)2 R3SiB(NR2)2 (87) R3SiBpin (88) Me3SnB(NR2)2 (90) Yield/% Ref.
1]nonane) . A selective cis-addition catalyzed by a palladium(0) complex affords 9-[(Z)-2-RS-1-alkenyl]-9-BBN (73), which exhibits exceptionally high reactivity on protonolysis with methanol , cross-coupling reaction with organic halides , and nucleophilic addition to carbonyl compounds . The ready availability of these boron reagents by catalytic hydroboration and thioboration may offer a flexible and reliable route to such stereodefined alkenyl sulfides in combination with numerous reactions reported in organoboron compounds.
Platinum(0) complexes analogously catalyze the addition of other (alkoxo)diborons, 81, 83 and 84, but the reaction of (Me2N)2BB(NM2)2 is very slow even at 120°C because of its slow oxidative addition to the platinum(0) complex. There are no large differences in the yields and the reaction rates between internal and terminal alkynes and the reaction is available with various functional groups. The carbon-carbon double bond, chloro, epoxy, ester, cyano, and ketone carbonyl groups remain intact during the addition to the C-C triple bonds .