Palladium-Catalyzed Chemoselective Synthesis of 2-Aminocinnamyl Esters via Sequential Amination and Olefination of Aryl Iodides.
Chen, Yanhui; Lv, Weiwei; Ba, Dan; Wen, Si; Cheng, Guolin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01695

data_4038874
_publ_section_title
;
 Palladium-Catalyzed Chemoselective Synthesis of 2-Aminocinnamyl Esters
 via Sequential Amination and Olefination of Aryl Iodides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01695
_journal_year                    2020
_chemical_formula_moiety         'C21 H27 N2 O6'
_chemical_formula_sum            'C21 H27 N2 O6'
_chemical_formula_weight         403.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                65.267(8)
_cell_angle_beta                 79.270(8)
_cell_angle_gamma                78.503(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1218(9)
_cell_length_b                   11.2194(10)
_cell_length_c                   13.0487(10)
_cell_measurement_reflns_used    2006
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0740
_cell_measurement_theta_min      4.6490
_cell_volume                     1051.20(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -22.00   4.00   1.00    3.90    --   15.65 -57.00 -90.00   26
  2  \w     -6.00  21.00   1.00    3.90    --  -16.51 -99.00-120.00   27
  3  \w     -8.00  22.00   1.00    3.90    --  -16.51 -99.00 -30.00   30
  4  \w    -52.00  30.00   1.00    3.90    --   15.65 -57.00 -30.00   82
  5  \w    -25.00   2.00   1.00    3.90    --  -16.51  38.00  90.00   27
  6  \w    -52.00  42.00   1.00    3.90    --   15.65 -77.00  90.00   94
  7  \w    -11.00  79.00   1.00    3.90    --   15.65  77.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0472710000
_diffrn_orient_matrix_UB_12      0.0641977000
_diffrn_orient_matrix_UB_13      -0.0178406000
_diffrn_orient_matrix_UB_21      -0.0694978000
_diffrn_orient_matrix_UB_22      -0.0261548000
_diffrn_orient_matrix_UB_23      -0.0047872000
_diffrn_orient_matrix_UB_31      -0.0313920000
_diffrn_orient_matrix_UB_32      -0.0114432000
_diffrn_orient_matrix_UB_33      0.0573498000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8268
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.4391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1733
_reflns_number_gt                2811
_reflns_number_total             4330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c01695_si_002.cif
_cod_data_source_block           exp_7388
_cod_original_cell_volume        1051.20(17)
_cod_database_code               4038874
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00a,H00b), C00J(H00c,H00d), C00K(H00h,H00i), C00L(H00j,H00k), C00N(H00l,
 H00m), C00O(H00n,H00o), C00P(H00p,H00q), C00R(H00s,H00t)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00E), C00F(H00F), C00G(H00G), C00Q(H00r)
2.c Idealised Me refined as rotating group:
 C00S(H00u,H00v,H00w), C00T(H00x,H00y,H)
;
_olex2_date_sample_data_collection 2019-10-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.705