Palladium-Catalyzed Vinylation of Aminals with Simple Alkenes: A New Strategy To Construct Allylamines
Yinjun Xie; Jianhua Hu; Yanyu Wang; Chungu Xia; Hanmin Huang; Journal of the American Chemical Society 134 (2012) 20613–20616; doi:10.1021/ja310848x

data_4119058
_publ_contact_author_name
;
;
_publ_section_title
;
 Palladium-Catalyzed Vinylation of Aminals with Simple Alkenes: A New
 Strategy To Construct Allylamines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20613
_journal_page_last               20616
_journal_paper_doi               10.1021/ja310848x
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C54 H48 N O P2 Pd, C F3 O3 S'
_chemical_formula_sum            'C55 H48 F3 N O4 P2 Pd S'
_chemical_formula_weight         1044.34
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_symmetry_space_group_name_Hall  '-I 2yc'
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
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_audit_creation_date             2012-10-19
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  Olex2 1.2
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_cell_angle_alpha                90.00
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_cell_length_a                   28.6790(4)
_cell_length_b                   15.9767(3)
_cell_length_c                   22.2674(5)
_cell_measurement_reflns_used    13407
_cell_measurement_temperature    281(4)
_cell_measurement_theta_max      72.4707
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      281(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9584
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_diffrn_measurement_details
;
  1 omega  -58.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 48

  2 omega  -81.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 44

  3 omega   -6.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 30

  4 omega -128.00 -102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000    0.0000 26

  5 omega -116.00  -90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000   90.0000 26

  6 omega -116.00  -73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000   60.0000 43

  7 omega  -64.00  -39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000   90.0000 25

  8 omega  -96.00    8.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   77.0000 -120.0000 104

  9 omega -132.00  -39.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000    0.0000   90.0000 93

 10 omega  -31.00   10.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000    0.0000   90.0000 41

 11 omega   48.00   74.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000    0.0000 26

 12 omega  101.00  134.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  120.0000 33

 13 omega  150.00  177.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  120.0000 27

 14 omega   47.00  141.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   60.0000 94

 15 omega   65.00  114.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 49

 16 omega   80.00  111.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -108.0000  -39.0000 31

 17 omega   50.00   79.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  150.0000 29

 18 omega   64.00  104.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -120.0000 40

 19 omega  145.00  178.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  120.0000 33

 20 omega  106.00  146.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  120.0000 40

 21 omega   80.00  106.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  120.0000 26

 22 omega  112.00  138.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  120.0000 26

 23 omega   46.00   92.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -150.0000 46

 24 omega   88.00  118.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  120.0000 30

 25 omega   57.00  123.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  150.0000 66

 26 omega   44.00   70.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  120.0000 26

 27 omega   60.00  113.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000 -150.0000 53

 28 omega   81.00  112.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -180.0000 31

 29 omega   75.00  101.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  120.0000 26

 30 omega   82.00  114.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000 -120.0000 32

 31 omega  127.00  153.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 26

 32 omega   75.00  101.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 26

 33 omega   60.00  145.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000    0.0000 85

 34 omega  108.00  134.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   90.0000 26

 35 omega   43.00   91.00   1.0000    2.8000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -60.0000 48
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0124091000
_diffrn_orient_matrix_UB_12      0.0925366000
_diffrn_orient_matrix_UB_13      -0.0116083000
_diffrn_orient_matrix_UB_21      -0.0016996000
_diffrn_orient_matrix_UB_22      0.0151990000
_diffrn_orient_matrix_UB_23      0.0681974000
_diffrn_orient_matrix_UB_31      0.0522603000
_diffrn_orient_matrix_UB_32      0.0224541000
_diffrn_orient_matrix_UB_33      0.0017711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29237
_diffrn_reflns_theta_full        72.65
_diffrn_reflns_theta_max         72.65
_diffrn_reflns_theta_min         3.97
_diffrn_source                   'SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    4.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78479
_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             4288
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     606
_refine_ls_number_reflns         9990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+8.4118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                8939
_reflns_number_total             9990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja310848x_si_001.cif
_cod_data_source_block           xieyj1018
_cod_database_code               4119058
_reflns_odcompleteness_completeness 95.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33