Palladium-Catalyzed Selective β-Arylation of Aliphatic Amides Using a Removable N,O-Bidentate Auxiliary
Zhang, Shou-Kun; Yang, Xin-Yan; Zhao, Xue-Mei; Li, Peng-Xiang; Niu, Jun-Long; Song, Mao-Ping; Organometallics 34 (2015) 4331–; doi:10.1021/acs.organomet.5b00581

data_4087760
_publ_section_title
;
 Palladium-Catalyzed Selective \b-Arylation of Aliphatic Amides Using a
 Removable N,O-Bidentate Auxiliary
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4331
_journal_paper_doi               10.1021/acs.organomet.5b00581
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C15 H17 N3 O2 Pd'
_chemical_formula_sum            'C15 H17 N3 O2 Pd'
_chemical_formula_weight         377.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.152(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3447(13)
_cell_length_b                   16.9532(17)
_cell_length_c                   10.2080(12)
_cell_measurement_reflns_used    2607
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.0572
_cell_measurement_theta_min      3.2021
_cell_volume                     1518.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    3.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104   19.0000    0.0000 42

  2 omega  -12.00   13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000  120.0000 25

  3 omega   -7.00   19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000  -60.0000 26

  4 omega  -43.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104   37.0000  150.0000 71

  5 omega  -25.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -99.0000  -60.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0696213000
_diffrn_orient_matrix_UB_12      0.0135732000
_diffrn_orient_matrix_UB_13      0.0492089000
_diffrn_orient_matrix_UB_21      -0.0302638000
_diffrn_orient_matrix_UB_22      0.0386953000
_diffrn_orient_matrix_UB_23      -0.0060359000
_diffrn_orient_matrix_UB_31      -0.0281483000
_diffrn_orient_matrix_UB_32      -0.0080605000
_diffrn_orient_matrix_UB_33      0.0549248000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6797
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.21
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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
;
;
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.0791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                2548
_reflns_number_total             3092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00581_si_002.cif
_cod_data_source_block           complex-7
_cod_database_code               4087760
_chemical_oxdiff_formula         C1H1O1N1Pd1
_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:
  H1 of C1, H2 of C2, H3 of C3, H4 of C4, {H8A,H8B} of C8, H11 of C11, H12 of
  C12, H13 of C13, H14 of C14, H15 of C15
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H10A,H10B,H10C} of C10
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;