Page 67 - 《精细化工》2023年第5期

第 5 期 宋晓楠，等: 金属基催化剂催化不饱和烃的硼氢化反应研究进展 ·987·

compounds[J]. Journal of the American Chemical Society, 2000, Journal of the American Chemical Society, 2017, 139(24): 8130-8133.
122(20): 4990-4991. [44] SINGH A, SHAFIEI-HAGHIGHI S, SMITH C R, et al. Hydroboration
[25] WANG K C, BATES R W. Rhodium-catalysed hydroboration of of alkenes and alkynes employing earth-abundant metal catalysts[J].
terminal alkynes using pinacolborane promoted by tri(2-furyl) Asian Journal of Organic Chemistry, 2019, 9(3): 416-420.
phosphine[J]. Synthesis, 2017, 49(12): 2749-2752. [45] DOCHERTY J H, PENG J, DOMINEY A P, et al. Activation and
[26] LYU Y Z, TORIUMI N, IWASAWA N. (Z)-Selective hydroboration discovery of earth-abundant metal catalysts using sodium
of terminal alkynes catalyzed by a PSP-pincer rhodium complex[J]. tert-butoxide[J]. Nature Chemistry, 2017, 9(6): 595-600.
Organic Letters, 2021, 23(23): 9262-9266. [46] ZHONG H Y, FRIEDFELD M R, CHIRIK P J. Syntheses and
[27] YOSHIDA H, KIMURA M, TANAKA H, et al. An anthranilamide- catalytic hydrogenation performance of cationic bis(phosphine)
substituted borane [H—B (aam)]: Its stability and application to cobalt(Ⅰ) diene and arene compounds[J]. Angewandte Chemie
iridium-catalyzed stereoselective hydroboration of alkynes[J]. International Edition, 2019, 58(27): 9194-9198.
Chemical Communications, 2019, 55(38): 5420-5422. [47] TOKMIC K, MARKUS C R, ZHU L, et al. Well-defined cobalt(Ⅰ)
[28] DING H, GAO W W, YU T, et al. Hydroboration and diboration of dihydrogen catalyst: Experimental evidence for a Co(Ⅰ)/Co(Ⅲ)
Internal alkynes under iridium catalysis[J]. Journal of Organic redox process in olefin hydrogenation[J]. Journal of the American
Chemistry, 2022, 87(2): 1526-1536. Chemical Society, 2016, 138(36): 11907-11913.
[29] CRUDDEN C M, HLEBA Y B, CHEN A C. Regio- and [48] MERZ L S, BLASIUS C K, WADEPOHL H, et al. Square planar
enantiocontrol in the room-temperature hydroboration of vinyl arenes cobalt( Ⅱ ) hydride versus T-shaped cobalt( Ⅰ ): Structural
with pinacol borane[J]. Journal of the American Chemical Society, characterization and dihydrogen activation with PNP-cobalt pincer
2004, 126(30): 9200-9201. complexes[J]. Inorganic Chemistry, 2019, 58(9): 6102-6113.
[30] CAI Y H, TAN D H, ZHANG Q Q, et al. Synthesis of [49] ZHANG G Q, LI S H, WU J, et al. Highly efficient and selective
difluoromethylated benzylborons via rhodium(Ⅰ)-catalyzed fluorine- hydroboration of terminal and internal alkynes catalysed by a
retainable hydroboration of Gem-difluoroalkenes[J]. Chinese cobalt(Ⅱ) coordination polymer[J]. Organic Chemistry Frontiers,
Chemical Letters, 2021, 32(1): 417-420. 2019, 6(18): 3228-3233.
[31] EVANS D A, FU G C, ANDERSON B A. Mechanistic study of the [50] GONZÁLEZ M J, BAUER F, BREIT B. Cobalt-catalyzed
rhodium( Ⅰ )-catalyzed hydroboration reaction[J]. Journal of the hydroboration of terminal and internal alkynes[J]. Organic Letters,
American Chemical Society, 1992, 114(17): 6679-6685. 2021, 23(21): 8199-8203.
[32] SMITH S M, THACKER N C, TAKACS J M. Efficient [51] BEN D H, ROCK C L, FLORES M, et al. Hydroboration of alkynes
amide-directed catalytic asymmetric hydroboration[J]. Journal of the and nitriles using an α-diimine cobalt hydride catalyst[J]. Chemical
American Chemical Society, 2008, 130(12): 3734-3735. Communications, 2017, 53(53): 7333-7336.
[33] SMITH S M, HOANG G L, PAL R, et al. γ-Selective directed [52] OBLIGACION J V, NEELY J M, YAZDANI A N, et al. Cobalt
catalytic asymmetric hydroboration of 1,1-disubstituted alkenes[J]. catalyzed Z-selective hydroboration of terminal alkynes and
Chemical Communications, 2012, 48(100): 12180-12182. elucidation of the origin of selectivity[J]. Journal of the American
[34] HOANG G L, YANG Z D, SMITH S M, et al. Enantioselective Chemical Society, 2015, 137(18): 5855-5858.
desymmetrization via carbonyl-directed catalytic asymmetric hydroboration [53] BLASIUS C K, VASILENKO V, MATVEEVA R, et al. Reaction
and Suzuki-Miyaura cross-coupling[J]. Organic Letters, 2015, 17(4): pathways and redox states in α-selective cobalt-catalyzed
940-943. hydroborations of alkynes[J]. Angewandte Chemie International
[35] HOANG G L, ZHANG S, TAKACS J M. Rhodium-catalyzed Edition, 2020, 59(51): 23010-23014.
asymmetric hydroboration of γ,δ-unsaturated amide derivatives: [54] CHEN J P, SHEN X Z, LU Z. Cobalt-catalyzed Markovnikov
δ-Borylated amides[J]. Chemical Communications, 2018, 54(38): selective sequential hydrogenation/hydrohydrazidation of aliphatic
4838-4841. terminal alkynes[J]. Journal of the American Chemical Society, 2020,
[36] ZHAO W, CHEN K Z, LI A Z, et al. Remote stereocenter through 142(34): 14455-14460.
amide-directed, rhodium-catalyzed enantioselective hydroboration of [55] CHENG Z Y, XING S P, GUO J, et al. Highly regioselective
unactivated internal alkenes[J]. Journal of the American Chemical sequential 1,1-dihydrosilylation of terminal aliphatic alkynes with
Society, 2022, 144(29): 13071-13078. primary silanes[J]. Chinese Journal of Chemistry, 2019, 37(5):
[37] WANG G Z, LIANG X Y, CHEN L L, et al. Iridium-catalyzed distal 457-461.
hydroboration of aliphatic internal alkenes[J]. Angewandte Chemie [56] GUO J, WANG H L, XING S P, et al. Cobalt-catalyzed asymmetric
International Edition, 2019, 58(24): 8187-8191. synthesis of Gem-bis(silyl)alkanes by double hydrosilylation of
[38] ZHAO H L, GAO Q, ZHANG Y J, et al. Iridium-catalyzed gamma- aliphatic terminal alkynes[J]. Chem, 2019, 5(4): 881-895.
selective hydroboration of gamma-substituted allylic amides[J]. [57] CHEN J P, SHEN X Z, LU Z. Cobalt-catalyzed Markovnikov-type
Organic Letters, 2020, 22(7): 2861-2866. selective hydroboration of terminal alkynes[J]. Angewandte Chemie
[39] KUCIŃSKI K, HRECZYCHO G. Hydrosilylation and hydroboration International Edition, 2021, 60(2): 690-694.
in a sustainable manner: From earth-abundant catalysts to catalyst- [58] WU J Y, MOREAU B, RITTER T. Iron-catalyzed 1,4-hydroboration
free solutions[J]. Green Chemistry, 2020, 22(16): 5210-5224. of 1,3-dienes[J]. Journal of the American Chemical Society, 2009,
[40] KAUR U, SAHA K, GAYEN S, et al. Contemporary developments 131(36): 12915-12917.
in transition metal boryl complexes: An overview[J]. Coordination [59] OBLIGACION J V, CHIRIK P J. Highly selective bis(imino)
Chemistry Reviews, 2021, 446: 214106 pyridine iron-catalyzed alkene hydroboration[J]. Organic Letters,
[41] HABERBERGER M, ENTHALER S. Straightforward iron-catalyzed 2013, 15(11): 2680-2683.
synthesis of vinylboronates by the hydroboration of alkynes[J]. [60] GREENHALGH M D, THOMAS S P. Chemo-, regio-, and
Chemistry-An Asian Journal, 2013, 8(1): 50-54. stereoselective iron-catalysed hydroboration of alkenes and
[42] NAKAJIMA K, KATO T, NISHIBAYASHI Y. Hydroboration of alkynes[J]. Chemical Communications, 2013, 49(95): 11230-11232.
alkynes catalyzed by pyrrolide-based PNP pincer-iron complexes[J]. [61] LIU Y, ZHOU Y H, WANG H, et al. FeCl 2-catalyzed hydroboration
Organic Letters, 2017, 19(16): 4323-4326. of aryl alkenes with bis(pinacolato)diboron[J]. RSC Advances, 2015,
[43] GORGAS N, ALVES L G, STOGER B, et al. Stable, yet highly 5(90): 73705-73713.
reactive nonclassical iron( Ⅱ ) polyhydride pincer complexes: [62] SU W, QIAO R X, JIANG Y Y, et al. Ligand-free iron-catalyzed
Z-Selective dimerization and hydroboration of terminal alkynes[J]. regioselectivity-controlled hydroboration of aliphatic terminal